CN109942578B - Organic compounds of heteroanthracene class, preparation method and application - Google Patents
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Abstract
The invention relates to the technical field of semiconductors, in particular to a heteroanthracene organic compound and a preparation method and application thereof. The structural formula of the heteroanthracene organic compound is shown in chemical formula 1:
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a heteroanthracene organic compound and a preparation method and application thereof.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device comprises electrode materials and organic functional materials clamped between different electrodes, and various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to the electrodes at the two ends of the organic functional material layer and positive and negative charges in the organic functional material layer are acted by an electric field, the positive and negative charges are further compounded in the light-emitting layer, and the OLED electroluminescence is generated.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different. Therefore, development of a functional material with a novel structure is very important.
Disclosure of Invention
The invention aims to provide a novel heteroanthracene organic compound, a preparation method and application thereof.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
a heteroanthracene organic compound has a structural formula shown in chemical formula 1:
wherein:
R1and R2Each independently represents a substituted or unsubstituted alkyl group having C1-C60, a cycloalkyl group having C3-C60, a substituted or unsubstituted alkenyl group having C2-C60, a cycloalkenyl group having C3-C60, a substituted or unsubstituted alkynyl group having C3-C60, a cycloalkynyl group having C3-C60, a substituted or unsubstituted aryl group having C6-C60, or a heterocyclic group having C6-C60;
R3and R4Each independently represent: hydrogen, isotopes of hydrogen, halogen, cyano, nitro, hydroxyl, amino, sulfonic acid, sulfonyl, phosphate, phosphoryl, substituted or unsubstituted silyl, boryl, phosphorus, substituted or unsubstituted alkyl groups from C1 to C60, cycloalkyl groups from C3 to C60, alkoxy, alkylamino, alkylmercapto, substituted or unsubstituted alkenyl groups from C2 to C60, cycloalkenyl groups from C3 to C60, substituted or unsubstituted alkynyl groups from C3 to C60, cycloalkynyl groups from C3 to C60, substituted or unsubstituted aryl groups from C6 to C60, or heterocyclic groups from C6 to C60; or an alicyclic or aromatic ring linked to an adjacent substituent to form a substituted or unsubstituted mono-or polycyclic C3-C30, whose carbon atom may be replaced with at least one hetero atom selected from nitrogen, oxygen, or sulfur;
m and n are integers of 0-4;
Ar1is a substituted or unsubstituted C5-C30 aromatic ring or a substituted or unsubstituted C5-C60 heterocyclic ring;
Ar2is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C1-C30 heteroaryl; or an alicyclic or aromatic ring linked to an adjacent substituent to form a mono-or polycyclic C3-C30, whose carbon atom may be replaced with at least one hetero atom selected from nitrogen, oxygen, or sulfur.
In the above-mentioned technical solutions, Ar is preferred1Is benzene ring, naphthalene ring, anthracene ring, pyrene ring or phenanthrene ring.
In the above-mentioned technical solutions, Ar is preferred2Is one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, furyl, thienyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, quinazoline, benzimidazole, acridine and derivatives thereof, oxazole, thiazole, phenothiazine, isopropyl and cyclohexyl.
In the above technical solution, Ar is further preferable2Is any one selected from the following structures:
wherein: r is hydrogen, halogen, cyano, C1-C30 alkyl, C6-C50 aryl, C7-C50 aralkyl, C7-C50 arylalkoxy, C7-C50 arylalkylmercapto or C5-C50 heteroaryl; and said-R represents any position on the phenyl ring on which it is located, "+" is the linking position.
In the above technical solution, the heteroanthracene organic compound is selected from any one of the following structures:
a method for preparing a heteroanthracene organic compound, comprising the following steps:
synthesis of intermediate C: under a nitrogen atmosphere, the raw materials B and NaOt-Bu were added to dry toluene and stirred for 20min, followed by the addition of raw material A, Pd (OAc)2And P (t-Bu)3Heating and then reacting; after the monitoring reaction is finished, cooling to room temperature, adding water for washing, layering, extracting, and separating by a silica gel chromatographic column to obtain an intermediate C; the reaction temperature is preferably 80 ℃, and the reaction time is 6 hours;
② synthesizing an intermediate E: dissolving the intermediate C in anhydrous tetrahydrofuran, cooling to about 0 ℃, dropwise adding a Grignard reagent D, and then heating for reaction; after the reaction is finished, cooling to normal temperature, adding water for washing, layering, extracting by using ethyl acetate, washing the obtained organic phase by using a saturated sodium bicarbonate water solution, drying, and separating by using a silica gel chromatographic column to obtain an intermediate E; the preferable reaction temperature is 40 ℃, and the reaction time is 6 h;
when the raw material B contains R1When the radical is the same, the Grignard reagent D is R2MgBr; when the raw material B contains R2When the radical is the same, the Grignard reagent D is R1MgBr；
Synthesis of intermediate F: dissolving the intermediate E in a dry mixed solvent of tetrahydrofuran and toluene, and adding methanesulfonic acid at normal temperature to react; after the reaction is finished, respectively adding water and ethyl acetate, stirring, layering, collecting an organic phase, washing with a saturated sodium bicarbonate water solution, drying, and removing an organic solvent to obtain an intermediate F; the preferable reaction time is 8 h;
synthesis of intermediate H: intermediate F and NaOt-Bu were added to dry toluene under nitrogen and stirred for 20min, followed by the addition of intermediate G, Pd (OAc)2And P (t-Bu)3Heating and then reacting; after the monitoring reaction is finished, cooling to room temperature, adding water for washing, layering, extracting, and separating by a silica gel chromatographic column to obtain an intermediate H; the reaction temperature is preferably 80 ℃, and the reaction time is 6 hours;
fifth, synthesizing an intermediate I: adding the intermediate H into triethyl phosphite, heating the reaction, and reacting; after the reaction is finished, cooling to room temperature, slowly adding the reaction liquid into ice water, separating out a large amount of solid, stirring for 1h, filtering, adding dichloromethane into the solid, stirring to dissolve the solid basically, adding petroleum ether to separate out the solid, stirring for 1h, filtering and drying to obtain an intermediate I; the reaction temperature is preferably 155 ℃, and the reaction time is 5 hours;
sixthly, synthesizing a final product shown in a chemical formula 1: intermediate I and NaOt-Bu were added to dry toluene under nitrogen and stirred for 20min, followed by the addition of intermediate J, Pd (OAc)2And P (t-Bu)3Heating and then reacting; after the monitoring reaction is finished, cooling to room temperature, adding water for washing, layering, extracting, and separating by a silica gel chromatographic column to obtain a final product shown in chemical formula 1; the reaction temperature is preferably 80 ℃, and the reaction time is 6 hours;
the synthetic route is as follows:
wherein: r1、R2、R3、R4、Ar1、Ar2M and n are in accordance with the ranges defined in chemical formula 1, and X is halogen.
The invention also provides application of the heteroanthracene organic compound in preparing an organic electroluminescent device. The organic electroluminescent device includes at least one functional layer containing the organic compound represented by the chemical formula 1.
The invention also provides an organic electroluminescent device which comprises an electron blocking layer, wherein the material of the electron blocking layer is an organic compound represented by the chemical formula 1.
The present invention also provides an organic electroluminescent device comprising a light emitting layer containing the organic compound represented by chemical formula 1.
The invention has the beneficial effects that:
compared with comparative device 1, the efficiency and the service life of the organic heteroanthracene compound provided by the invention are greatly improved compared with those of the known OLED material, and especially the service life attenuation of the device is greatly improved.
The preparation method of the organic heteroanthracene compound provided by the invention is simple and easy to implement, has high yield and is suitable for industrial production.
Detailed Description
Example 1: synthesis of Compound 1
2-aminobenzophenone (19.7g, 100mmol) and NaOt-Bu (19.2g, 200mmol) were added to 200mL dry toluene under a nitrogen atmosphere and stirred for 20min, followed by bromobenzene (15.6g, 100mmol), Pd (OAc)2(0.2g, 1mmol) and P (t-Bu)3(0.8g, 2mmol), and the reaction was carried out at 80 ℃ for 6 hours. After the reaction was monitored, the reaction mixture was cooled to room temperature,and adding 300mL of water for washing, layering, extracting and separating by using a silica gel chromatographic column to obtain the compound C-124.58g with the yield of 90%.
Dissolving the intermediate C-1(24.58g and 90mmol) in 300mL of anhydrous tetrahydrofuran, cooling to about 0 ℃, dropwise adding a phenylmagnesium bromide solution (44mL and 110mmol), and raising the temperature to 40 ℃ for reaction for 6 h. After the reaction is finished, cooling to normal temperature, adding 300mL of water for washing, demixing, extracting with 300mL of ethyl acetate, washing the obtained organic phase with saturated sodium bicarbonate water solution, drying, and separating by a silica gel chromatographic column to obtain an intermediate E-125.28g with the yield of 80%.
Intermediate E-1(25.28g, 72mmol) was dissolved in a dry mixed solvent of 150mL tetrahydrofuran and 150mL toluene, and methanesulfonic acid (34.56g, 360mmol) was added at room temperature and reacted for 8 h. After the reaction, 300mL of water and ethyl acetate were added, respectively, and the mixture was stirred and layered, and the organic phase was collected, washed with a saturated aqueous solution of sodium bicarbonate, dried and the organic solvent was removed to obtain intermediate F-122.79g with a yield of 95%.
Intermediate F-1(22.79G, 72mmol) and NaOt-Bu (13.8G, 144mmol) were added to 200mL dry toluene under nitrogen and stirred for 20min, followed by intermediate G-1(14.47G, 72mmol), Pd (OAc)2(0.14g, 0.72mmol) and P (t-Bu)3(0.58g, 1.44mmol), and the temperature is raised to 80 ℃ for reaction for 6 h. After the reaction is monitored, the reaction product is cooled to room temperature, 300mL of water is added for washing, layering and extraction, and silica gel chromatographic column separation is carried out to obtain intermediate H-127.8g with the yield of 85%.
Intermediate H-1(27.8g 61.2mmol) was added to 140mL triethyl phosphite and the reaction heated to 155 ℃ for 5 hours. After the reaction, the reaction mixture was cooled to room temperature. Slowly adding the reaction solution into 1L of ice water, precipitating a large amount of solid, stirring for 1h, filtering, adding 100mL of dichloromethane into the solid, stirring to dissolve the solid basically, adding 500mL of petroleum ether to precipitate the solid, stirring for 1h, filtering and drying. Intermediate I-119.38g was obtained in 75% yield.
Intermediate I-1(19.38g, 45.9mmol) and NaOt-Bu (8.8g, 91.8mmol) were added to 200mL dry toluene under nitrogen and stirred for 20min, followed by bromobenzene (7.16g, 45.9mmol), Pd (OAc)2(0.092g, 0.46mmol) and P (t-Bu)3(0.368g, 0.92mmol), and the reaction was allowed to proceed for 6h at 80 ℃. After the reaction was monitored, the reaction mixture was cooled to room temperature, and 300mL of water was added to wash, separate layers, extract, and separate with a silica gel column to obtain 118.75g of compound with a yield of 82%. ESI-MS (M/z) (M +): theoretical value is 498.21, found 498.34.
Example 2: synthesis of Compound 2
Compound 2 was prepared according to the procedure for compound 1 in example 1. Except that intermediate J-1 in example 1 was changed to intermediate J-2 (tetrabromobiphenyl), the rest was the same, to obtain compound 2 in a yield of 78%. ESI-MS (M/z) (M +): theoretical value is 574.24, found 574.54.
Example 3: synthesis of Compound 10
Compound 10 was prepared according to the procedure for compound 1 in example 1. Except that intermediate J-1 in example 1 was changed to intermediate J-10 (3-bromo-9 phenylcarbazole), and the rest was the same, compound 10 was obtained in 80% yield. ESI-MS (M/z) (M +): theoretical value is 663.27, found 663.74.
Example 4: synthesis of Compound 14
Compound 14 was prepared according to the procedure for compound 1 in example 1. Except that the starting material B-1 was changed to the starting material B-14 and the format reagent D-1 was changed to D-14 in example 1, and the remainder was the same, compound 14 was obtained in a yield of 75%. ESI-MS (M/z) (M +): theoretical value is 506.24, found 506.34.
Example 5: synthesis of Compound 18
Compound 18 was prepared according to the procedure for compound 1 in example 1. Except that intermediate J-1 in example 1 was changed to intermediate J-18, and the rest was the same. Yield of compound 18 was 83% ESI-MS (M/z) (M +): theoretical value is 690.28, found 690.24.
Example 6: synthesis of Compound 32
Compound 32 was prepared according to the procedure for compound 1 in example 1. Except that the starting material B-1 was changed to B-32 and J-1 was changed to intermediate J-32 in example 1, and the rest was the same, compound 32 was obtained in a yield of 76%. ESI-MS (M/z) (M +): theoretical value is 672.26, found 672.28.
Example 7: synthesis of Compound 49
Compound 49 was prepared according to the procedure for compound 32 in example 6. Except that intermediate J-32 in example 6 was changed to J-49, and the rest was the same, compound 49 was obtained in 79% yield. ESI-MS (M/z) (M +): theoretical value is 638.24, found 638.58.
Example 8: synthesis of Compound 54
Compound 54 was prepared according to the procedure for compound 32 in example 6. Except that intermediate J-32 in example 6 was changed to J-54, and the rest was the same, compound 54 was obtained in a yield of 81%. ESI-MS (M/z) (M +): theoretical value is 625.25, found 625.36.
Example 9: synthesis of Compound 70
Compound 70 was prepared according to the procedure for compound 32 in example 6. Except that intermediate J-32 in example 6 was changed to J-70 and the rest were the same. Compound 70 yield 79% ESI-MS (M/z) (M +): theoretical value is 740.29, found 740.86.
Example 10: synthesis of Compound 72
Compound 72 was prepared according to the procedure for compound 32 in example 6. Except that intermediate J-32 in example 6 was changed to J-72 and the rest was the same, compound 72 was obtained in 84% yield. ESI-MS (M/z) (M +): theoretical value is 755.33, found 755.36.
Example 11: synthesis of Compound 84
Compound 84 was prepared according to the procedure for compound 1 in example 1. Except that the starting material B-1 was changed to B-84 and J-1 was changed to intermediate J-84 in example 1, and the same was true for the rest, compound 84 was obtained in a yield of 74%. ESI-MS (M/z) (M +): theoretical value is 878.34, found 878.18.
Example 12: synthesis of Compound 90
Compound 90 was prepared according to the procedure for compound 1 in example 1. Except that the starting material B-1 and the Grignard reagent D-1 in example 1 were changed to B-90 and D-84, respectively, and the same applies to obtain the compound 90 in a yield of 84%. ESI-MS (M/z) (M +): theoretical value is 664.29, found 664.78.
Example 13: synthesis of Compound 92
Compound 92 was prepared according to the procedure for compound 1 in example 1. Except that the starting material B-1 in example 1 was changed to B-92, the intermediate G-1 was changed to the starting material G-92, and the intermediate J-1 was changed to J-92, which were otherwise the same. Yield of compound 92 was obtained 81% ESI-MS (M/z) (M +): theoretical value is 748.29, found 748.79.
Thermal decomposition temperatures (Td) of the compounds synthesized in examples 1 to 13 and of the known host compound CBP were measured by thermogravimetric analysis. The glass transition temperature (Tg) of the above compounds was measured using differential scanning calorimetry. The results are shown in table 1:
TABLE 1
| Compound (I) | Td(℃) | Tg(℃) |
| 1 | 433 | 142 |
| 2 | 421 | 145 |
| 10 | 419 | 150 |
| 14 | 427 | 146 |
| 18 | 419 | 151 |
| 32 | 426 | 147 |
| 49 | 440 | 144 |
| 54 | 438 | 152 |
| 70 | 427 | 148 |
| 72 | 435 | 146 |
| 84 | 426 | 141 |
| 90 | 417 | 150 |
| 92 | 426 | 143 |
| CBP | 342 | 98 |
Device example 1: an electroluminescent device, which is prepared by the steps comprising:
cleaning the ITO anode layer on the transparent substrate layer, respectively ultrasonically cleaning the ITO anode layer with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer in a plasma cleaner for 2 minutes; b) evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer; c) evaporating a hole transport material NPB on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 60nm, and the hole transport layer is a hole transport layer; d) a light-emitting layer was deposited on the hole-transporting layer by evaporation, using the compound 1 of example 1 as a host material, Ir (ppy)3As doping material, Ir (ppy)3And compound 1 in a mass ratio of 5: 9:5, thickness of 30 nm; f) evaporating an electron transport material TPBI on the light-emitting layer in a vacuum evaporation mode, wherein the thickness is 40 nm; g) vacuum evaporating an electron injection layer LiF on the electron transport layer, wherein the thickness of the electron injection layer LiF is 1nm, and the electron injection layer is the electron injection layer; h) and (3) vacuum evaporating cathode Al (100nm) on the electron injection layer, wherein the cathode Al is a cathode reflecting electrode layer, and the electroluminescent device is manufactured.
Device example 2: this embodiment differs from device embodiment 1 in that: the host material of the luminescent layer of the electroluminescent device is the compound 2.
Device example 3: this embodiment differs from device embodiment 1 in that: the host material of the luminescent layer of the electroluminescent device is the compound 10 of the invention.
Device example 4: this embodiment differs from device embodiment 1 in that: the host material of the luminescent layer of the electroluminescent device is the compound 14 of the invention.
Device example 5: this embodiment differs from device embodiment 1 in that: the host material of the luminescent layer of the electroluminescent device is the compound 18 of the invention.
Device example 6: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the electroluminescent device is the compound 32 of the invention.
Device example 7: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the electroluminescent device is the compound 49 of the present invention.
Device example 8: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the electroluminescent device is the compound 54 of the present invention.
Device example 9: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the electroluminescent device is the compound 70 of the present invention.
Device example 10: this example differs from device example 1 in that the host material of the light-emitting layer of the electroluminescent device is the compound 72 of the present invention.
Device example 11: this example differs from device example 1 in that the host material of the light-emitting layer of the electroluminescent device is the compound 84 of the invention.
Device example 12: this example differs from device example 1 in that the host material of the light-emitting layer of the electroluminescent device is the compound 90 of the present invention.
Device example 13: this example differs from device example 1 in that the host material of the light-emitting layer of the electroluminescent device is the compound 92 of the present invention.
Device comparative example 1: this example differs from device example 1 in that the host material of the light emitting layer of the electroluminescent device is CBP.
The electroluminescent properties of the manufactured OLEDs are shown in table 2.
TABLE 2
| Compound (I) | Current efficiency | Color(s) | LT95 Life | |
| Example 1 | 1 | 1.8 | Green colour | 9.2 |
| Example 2 | 2 | 2.0 | Green colour | 9.1 |
| Example 3 | 10 | 1.9 | Green colour | 9.0 |
| Example 4 | 14 | 2.3 | Green colour | 9.4 |
| Example 5 | 18 | 2.1 | Green colour | 9.5 |
| Example 6 | 32 | 2.5 | Green colour | 9.4 |
| Example 7 | 49 | 2.4 | Green colour | 9.7 |
| Example 8 | 54 | 1.9 | Green colour | 9.5 |
| Example 9 | 70 | 2.1 | Green colour | 9.9 |
| Example 10 | 72 | 2.4 | Green colour | 9.7 |
| Example 11 | 84 | 2.6 | Green colour | 9.2 |
| Example 12 | 90 | 2.4 | Green colour | 9.1 |
| Example 13 | 92 | 2.2 | Green colour | 9.0 |
| Comparative example 1 | CBP | 1.0 | Green colour | 1.0 |
The device test performance is referred to comparative example 1, and each performance index of the device of comparative example 1 is set to 1.0. Current efficiency of comparative example 1 was 28cd/A (@10 mA/cm)2) (ii) a LT95 lifetime decay was 2.5Hr at 5000 brightness.
The results in the table show that the organic compound of the present invention can be applied to the fabrication of an OLED light emitting device, and compared with comparative device example 1, the efficiency and lifetime of the organic compound are greatly improved compared with those of the known OLED material, and especially the lifetime decay of the device is greatly improved.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (6)
1. An organic heteroanthracene compound selected from any one of the following structures:
2. a process for the preparation of the heteroanthracene organic compound according to claim 1, comprising the following steps:
synthesis of intermediate C: under a nitrogen atmosphere, the raw materials B and NaOt-Bu were added to toluene, stirred, and then the raw material A, Pd (OAc) was added2And P (t-Bu)3Heating and then reacting; after the monitoring reaction is finished, cooling to room temperature, adding water for washing, layering, extracting, and separating by a silica gel chromatographic column to obtain an intermediate C;
② synthesizing an intermediate E: dissolving the intermediate C in anhydrous tetrahydrofuran, and dropwise adding a Grignard reagent DR2MgBr or R1MgBr, then heating to react; after the reaction is finished, cooling to normal temperature, adding water for washing, layering, extracting by using ethyl acetate, washing the obtained organic phase by using a saturated sodium bicarbonate water solution, drying, and separating by using a silica gel chromatographic column to obtain an intermediate E;
synthesis of intermediate F: dissolving the intermediate E in a mixed solvent of tetrahydrofuran and toluene, and adding methanesulfonic acid at normal temperature to react; after the reaction is finished, respectively adding water and ethyl acetate, stirring, layering, collecting an organic phase, washing with a saturated sodium bicarbonate water solution, drying, and removing an organic solvent to obtain an intermediate F;
synthesis of intermediate H: under a nitrogen atmosphere, intermediate F and NaOt-Bu were added to toluene with stirring, followed by the addition of intermediate G, Pd (OAc)2And P (t-Bu)3Heating and then reacting; after the monitoring reaction is finished, cooling to room temperature, adding water for washing, layering, extracting, and separating by a silica gel chromatographic column to obtain an intermediate H;
fifth, synthesizing an intermediate I: intermediate H was added to P (OEt)3Heating the reaction and then reacting; after the reaction is finished, cooling to room temperature, adding the reaction solution into ice water, separating out a large amount of solids, stirring, filtering, adding dichloromethane into the solids, stirring to dissolve the solids, adding petroleum ether to separate out the solids, stirring, filtering, and drying to obtain an intermediate I;
sixthly, synthesizing a final product shown in a chemical formula 1: intermediate I and NaOt-Bu were added to dry toluene under nitrogen and stirred, followed by the addition of intermediate J, Pd (OAc)2And P (t-Bu)3Heating and then reacting; after the monitoring reaction is finished, cooling to room temperature, adding water for washing, layering, extracting, and separating by a silica gel chromatographic column to obtain a final product shown in chemical formula 1;
the synthetic route is as follows:
wherein X is halogen; r1-R4，m，n，Ar1，Ar2Corresponding to the substituents on the respective compounds of claim 1.
3. Use of the heteroanthracene organic compound according to claim 1 or prepared according to claim 2 for the preparation of an organic electroluminescent device.
4. Use according to claim 3, wherein the organic electroluminescent device comprises at least one functional layer comprising an organic compound of the anthracene type according to claim 1 or prepared by the process according to claim 2.
5. Use according to claim 3, wherein the organic electroluminescent device comprises an electron blocking layer, and the electron blocking layer is made of an organic compound of the anthracene type according to claim 1 or prepared by the method according to claim 2.
6. Use according to claim 3, wherein the organic electroluminescent device comprises a light-emitting layer comprising an organic compound of the anthracene type according to claim 1 or prepared by a process according to claim 2.
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