CN112341465A - Novel polyheterocyclic compound and application thereof - Google Patents

Novel polyheterocyclic compound and application thereof Download PDF

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CN112341465A
CN112341465A CN202011196584.6A CN202011196584A CN112341465A CN 112341465 A CN112341465 A CN 112341465A CN 202011196584 A CN202011196584 A CN 202011196584A CN 112341465 A CN112341465 A CN 112341465A
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unsubstituted
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CN112341465B (en
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范洪涛
赵风月
梁现丽
温洁
陈婷
杭德余
段陆萌
班全志
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

The invention belongs to the technical field of organic electroluminescent display, and particularly relates to a novel polyheterocyclic compound and application thereof. A novel polyheterocyclic compound has a structure shown as a general formula I. The mother nucleus of the multi-heterocyclic compound has an electron-withdrawing effect, is connected with five-membered heterocyclic groups such as carbazole, furan, thiophene and the like with electron-donating capacity, can be used as a green light main body material, has good thermal stability and can be well applied to OLED devices.

Description

Novel polyheterocyclic compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent display, and particularly relates to a novel polyheterocyclic compound and application thereof.
Background
The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has wider application prospect.
The phosphorescent material has strong spin-orbit coupling effect, and can simultaneously utilize singlet excitons and triplet excitons, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100 percent. However, phosphorescent materials have a longer excited state lifetime, and are prone to form triplet-triplet quenching and triplet-polaron- quenching when the triplet exciton concentration is higher; phosphorescent materials are often incorporated as guest into host materials to reduce self-concentration quenching processes. Therefore, it is also an important matter to select a suitable host material in Phosphorescent organic electroluminescent devices (Ph OLEDs). Essential characteristics of the host material: (1) the high triplet state energy level is possessed; (2) the carrier mobility is better and can be matched with the energy level of the adjacent layer; (3) has high thermal stability and film forming stability.
Therefore, a stable and efficient main body material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the method has important practical application value.
Disclosure of Invention
The invention aims to provide an OLED main body material which has higher triplet state energy level, better carrier mobility, energy level matching with adjacent layers, better thermal stability and film forming stability, and application of the organic material in an OLED device.
In particular, the invention finds a novel class of compounds with a multi-heterocyclic structure which can be used for organic electroluminescent devices. The parent nucleus of the series of compounds has an electron-withdrawing effect, is connected with five-membered heterocyclic groups such as carbazole, furan, thiophene and the like with electron-donating capability, can be used as a green light main body material, has good thermal stability and can be well applied to OLED devices. The compound is represented by a general formula (I), and can be applied to OLED devices to achieve the purpose.
The first purpose of the invention is to provide a novel polyheterocyclic compound, which has a structure shown as a general formula I:
Figure BDA0002754186920000021
in the general formula (I), R1～R8At least one group in the aromatic group is an aromatic group containing a five-membered heterocycle, and the aromatic group containing the five-membered heterocycle is connected with a mother nucleus shown in a general formula (I) through a C atom; the remaining groups each independently represent a hydrogen atom, a halogen, a linear or branched alkyl group, a cycloalkyl group, an amino group, an alkylamino group, a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring.
Preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle contains at least one five-membered heterocycle, preferably one, two or three five-membered heterocycles; the five-membered heterocyclic ring contains at least one heteroatom, preferably one, two or three heteroatoms; the heteroatom is optionally selected from the group consisting of N atoms, S atoms, and O atoms; when the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains a plurality of hetero atoms, the respective hetero atoms may be the same as each other, may be partially the same as each other, or may be different from each other.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from: substituted or unsubstituted carbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl.
In a preferred embodiment of the present invention, in the substituted aromatic group containing a five-membered heterocycle, the substituent may be optionally selected from: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, indolo (e.g., N-benzaindolo), benzothieno, benzofuro. The number of the substituents is selected from 1 to 5, preferably an integer of 1 to 3.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002754186920000022
Figure BDA0002754186920000031
Figure BDA0002754186920000041
more preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure BDA0002754186920000042
Figure BDA0002754186920000051
further preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from the group consisting of:
Figure BDA0002754186920000052
Figure BDA0002754186920000061
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
In a preferred embodiment of the present invention, the compound is selected from the group consisting of compounds represented by the following general formulae I-1 to I-130:
Figure BDA0002754186920000062
Figure BDA0002754186920000071
Figure BDA0002754186920000081
Figure BDA0002754186920000091
Figure BDA0002754186920000101
Figure BDA0002754186920000111
Figure BDA0002754186920000121
Figure BDA0002754186920000131
Figure BDA0002754186920000141
the organic compound takes a multi-heterocyclic ring structure as a mother core, the mother core structure has good thermal stability and appropriate HOMO and LUMO energy levels and Eg, and OLED materials with a novel structure are obtained by introducing groups with electron donating capability into active positions in the mother core structure, namely introducing five-membered heterocyclic ring structures such as carbazole, furan, thiophene and the like with electron donating capability into the structure. The organic light emitting diode is applied to an OLED device and used as a green light main body material, the photoelectric property of the device can be effectively improved, and the device can be applied to the field of display or illumination.
The second purpose of the invention is to provide the application of the multi-heterocyclic compound shown in the general formula I in the organic electroluminescent device. Preferably, the organic compound is used as a luminescent host material of an electroluminescent layer in an organic electroluminescent device; further preferably, the light emitting host material is a green host material. The thickness of the electroluminescent layer can be 10-50 nm, and preferably 20-40 nm.
It is a third object of the present invention to provide an organic electroluminescent device comprising an electroluminescent layer comprising the compound according to the present invention.
As a preferred embodiment of the present invention, the organic electroluminescent device sequentially comprises, from bottom to top, a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer (including the organic material described in formula I), an electron transport layer, an electron injection layer, and a cathode layer. Preferably, the thickness of the electroluminescent layer can be 10 to 50nm, preferably 20 to 40 nm.
It is a fourth object of the present invention to provide a display apparatus including the organic electroluminescent device.
A fifth object of the present invention is to provide a lighting device including the organic electroluminescent device.
The novel OLED material provided by the invention takes a multi-heterocyclic structure compound as a mother nucleus, and an electron-donating group is introduced into the structure of the mother nucleus, so that the novel OLED material which has a high triplet state energy level, a good carrier mobility, a high thermal stability and a high film forming stability and can be matched with the energy level of an adjacent layer is obtained. The material can be applied to the field of organic electroluminescence, can be used as a green light main body material, and can effectively improve the photoelectric property of a device.
Detailed Description
The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting a suitable catalyst and a suitable solvent, and determining a suitable reaction temperature, a suitable reaction time, a suitable material ratio, and the like, which are not particularly limited in the present invention. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
Example 1 Synthesis of intermediate M1
Figure BDA0002754186920000151
The synthetic route is as follows:
Figure BDA0002754186920000152
the method comprises the following specific steps:
(1) adding 4, 6-dichloroisobenzofuran-1, 3-dione (21.7g, 0.1mol), 4-chlorobenzene-1, 2-diamine (21.3g, 0.15mol) and water (100mL) into a 1L reaction bottle with mechanical stirring, heating to 100 ℃, stirring, protecting with nitrogen, reacting at the temperature for 2 hours, and generating a light yellow solid after the reaction is finished;
(2) the precipitate was filtered, transferred to a test tube, warmed to 300 ℃, heated at atmospheric pressure for 1 hour, and then subjected to sublimation at 170 ℃ under vacuum, to isolate 25.8g of intermediate M1 as a white solid in about 80% yield.
Product MS (m/e): 321; elemental analysis (C)14H5Cl3N2O): theoretical value C: 51.97%, H: 1.56%, N: 8.66 percent; found value C: 51.83%, H: 1.68%, N: 8.46 percent.
Example 2: synthesis of intermediate M2
Figure BDA0002754186920000153
By using
Figure BDA0002754186920000154
Instead of the former
Figure BDA0002754186920000155
The intermediate M2 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 287; elemental analysis (C)14H6Cl2N2O): theoretical value C: 58.16%, H: 2.09%, N: 9.69 percent; found value C: 58.36%, H: 2.29%, N: 9.57 percent.
Example 3: synthesis of intermediate M3
Figure BDA0002754186920000161
By using
Figure BDA0002754186920000162
Respectively replace
Figure BDA0002754186920000163
The intermediate M3 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 287; elemental analysis (C)14H6Cl2N2O): theoretical value C: 58.16%, H: 2.09%, N: 9.69 percent; found value C: 58.29%, H: 2.27%, N: 9.58 percent.
Example 4: synthesis of intermediate M4
Figure BDA0002754186920000164
By using
Figure BDA0002754186920000165
Respectively replace
Figure BDA0002754186920000166
The intermediate M4 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 287; elemental analysis (C)14H6Cl2N2O): theoretical value C: 58.16%, H: 2.09%, N: 9.69 percent; found value C: 58.32%, H: 2.31%, N: 9.46 percent.
Example 5: synthesis of intermediate M5
Figure BDA0002754186920000167
By using
Figure BDA0002754186920000168
Respectively replace
Figure BDA0002754186920000169
The intermediate M5 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 254; elemental analysis (C)14H7ClN2O): theoretical value C: 66.03%, H: 2.77%, N: 11.00 percent; found value C: 66.23%, H: 2.63%, N: 11.16 percent.
Example 6: synthesis of intermediate M6
Figure BDA0002754186920000171
By using
Figure BDA0002754186920000172
Respectively replace
Figure BDA0002754186920000173
The intermediate M6 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 254; elemental analysis (C)14H7ClN2O): theoretical value C: 66.03%, H: 2.77%, N: 11.00 percent; found value C: 66.18%, H: 2.89%, N: 11.19 percent.
Example 7: synthesis of intermediate M7
Figure BDA0002754186920000174
By using
Figure BDA0002754186920000175
Instead of the former
Figure BDA0002754186920000176
The intermediate M7 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 254; elemental analysis (C)14H7ClN2O): theoretical value C: 66.03%, H: 2.77%, N: 11.00 percent; found value C: 66.21%, H: 2.97%, N: 11.20 percent.
Example 8: synthesis of intermediate M8
Figure BDA0002754186920000177
By using
Figure BDA0002754186920000181
Instead of the former
Figure BDA0002754186920000182
The intermediate M8 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 287; elemental analysis (C)14H6Cl2N2O): theoretical value C: 58.16%, H: 2.09%, N: 9.69 percent; found value C: 58.28%, H: 2.20%, N: 9.53 percent.
Example 9: synthesis of intermediate M9
Figure BDA0002754186920000183
By using
Figure BDA0002754186920000184
Instead of the former
Figure BDA0002754186920000185
The intermediate M9 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 287; elemental analysis (C)14H6Cl2N2O): theoretical value C: 58.16%, H: 2.09%, N: 9.69 percent; found value C: 58.04%, H: 2.30%, N: 9.87 percent.
Example 10: synthesis of intermediate M10
Figure BDA0002754186920000186
By using
Figure BDA0002754186920000187
Respectively replace
Figure BDA0002754186920000188
The intermediate M10 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 331; elemental analysis (C)14H6ClBrN2O): theoretical value C: 50.41%, H: 1.81%, N: 8.40 percent; found value C: 50.61%, H: 1.70%, N: 8.56 percent.
Example 11
Figure BDA0002754186920000191
Synthesis of (Compound I-13)
The synthetic route is as follows:
Figure BDA0002754186920000192
the method comprises the following specific steps:
synthesis of Compound I-13
A 1L three-necked flask is matched with magnetic stirring, M1(32.4g, 0.1mol), naphtho [2,3-b ] benzofuran-3-yl boric acid (78.7g, 0.3mol), cesium carbonate (117g, 0.36mol) and dioxane 400ml are sequentially added after nitrogen replacement, and stirring is started; after nitrogen replacement again, (2.2g, 11mmol) tri-tert-butylphosphine and (4.1g, 4.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 69.5g of pale yellow solid with the yield of about 80%.
Product MS (m/e): 868; elemental analysis (C)62H32N2O4): theoretical value C: 85.70%, H: 3.71%, N: 3.22%,; found value C: 85.88%, H: 3.86%, N: 3.42 percent.
Example 12
Figure BDA0002754186920000193
Synthesis of (Compound I-9)
The synthetic route is as follows:
Figure BDA0002754186920000201
synthesis of Compound I-9
The appropriate material ratio was chosen by substituting M1 with M2 and the other raw materials and procedures were the same as in example 11 to give 53.5g of a pale yellow solid with a yield of about 82%.
Product MS (m/e): 652; elemental analysis (C)46H24N2O3): theoretical value C: 84.65%, H: 3.71%, N: 4.29 percent; found value C: 84.85%, H: 3.88%, N: 4.49 percent.
Example 13
Figure BDA0002754186920000202
Synthesis of (Compound I-20)
The synthetic route is as follows:
Figure BDA0002754186920000203
the method comprises the following specific steps:
synthesis of Compound I-20
M3 was used in place of M1 and benzo [ b ] naphtho [1,2-d ] thiophen-10-ylboronic acid was used in place of naphtho [2,3-b ] benzofuran-3-ylboronic acid, and the other raw materials and procedures were the same as in example 11, except that the appropriate material ratios were selected, to obtain 54.1g of a pale yellow solid with a yield of about 79%.
Product MS (m/e): 684; elemental analysis (C)46H24N2OS2): theoretical value C: 80.68%, H: 3.53%, N: 4.09%; found value C: 80.88%, H: 3.33%, N: 4.29 percent.
Example 14
Figure BDA0002754186920000211
Synthesis of (Compound I-29)
The synthetic route is as follows:
Figure BDA0002754186920000212
synthesis of Compound I-29
M4 was used in place of M1, (10-phenyl-10H-phenanthrene [9,10-b ] carbazol-13-yl) boronic acid was used in place of naphtho [2,3-b ] benzofuran-3-ylboronic acid, and the other raw materials and procedures were the same as in example 11, selecting an appropriate material ratio, to give 77.2g of a pale yellow solid with a yield of about 77%.
Product MS (m/e): 1002; elemental analysis (C)74H42N4O): theoretical value C: 88.60%, H: 4.22%, N: 5.59 percent; found value C: 88.80%, H: 4.42%, N: 5.79 percent.
Example 15
Figure BDA0002754186920000213
Synthesis of (Compound I-32)
The synthetic route is as follows:
Figure BDA0002754186920000214
the method comprises the following specific steps:
synthesis of Compound I-32
Using M5 in place of M1 and (9-phenyl-9H-dibenzo [ a, c ] carbazol-12-yl) boronic acid in place of naphtho [2,3-b ] benzofuran-3-ylboronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 11 to give 43.8g of a pale yellow solid with a yield of about 78%.
Product MS (m/e): 561; elemental analysis (C)40H23N3O): theoretical value C: 85.54%, H: 4.13%, N: 7.48 percent; found value C: 85.74%, H: 4.33%, N: 7.59 percent.
Example 16
Figure BDA0002754186920000221
Synthesis of (Compound I-47)
The synthetic route is as follows:
Figure BDA0002754186920000222
the method comprises the following specific steps:
synthesis of Compound I-47
Using M6 instead of M1, (4- (9H-phenanthrene [4,5-abc ] carbazol-9-yl) phenyl) boronic acid instead of naphtho [2,3-b ] benzofuran-3-ylboronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 11 to give 49.1g of a pale yellow solid with a yield of about 84%.
Product MS (m/e): 585; elemental analysis (C)42H23N3O): theoretical value C: 86.13%, H: 3.96%, N: 7.17 percent; found value C: 86.33%, H: 3.76%, N: 7.37 percent.
Example 17
Figure BDA0002754186920000223
Synthesis of (Compound I-58)
The synthetic route is as follows:
Figure BDA0002754186920000231
the method comprises the following specific steps:
synthesis of Compound I-58
Using M7 in place of M1, (4- (10-phenylindol [3,2-b ] indol-5 (10H) -yl) phenyl) boronic acid in place of naphtho [2,3-b ] benzofuran-3-yl boronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 11 to give 45.5g of a pale yellow solid in about 79% yield.
Product MS (m/e): 576; elemental analysis (C)40H24N4O): theoretical value C: 83.31%, H: 4.20%, N: 9.72 percent; found value C: 83.51%, H: 4.40%, N: 9.88 percent.
Example 18
Figure BDA0002754186920000232
Synthesis of (Compound I-68)
The synthetic route is as follows:
Figure BDA0002754186920000233
the method comprises the following specific steps:
synthesis of Compound I-68
Using M8 instead of M1, (12-phenyl-12H-benzofuran [2,3-a ] carbazol-3-yl) boronic acid instead of naphtho [2,3-b ] benzofuran-3-yl boronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 11 to give 71.5g of a pale yellow solid with a yield of about 81%.
Product MS (m/e): 882; elemental analysis (C)62H34N4O3): theoretical value C: 84.34%, H: 3.88%, N: 6.35 percent; found value C: 84.54%, H: 3.68%, N: 6.48 percent.
Example 19
Figure BDA0002754186920000241
Synthesis of (Compound I-89)
The synthetic route is as follows:
Figure BDA0002754186920000242
the method comprises the following specific steps:
synthesis of Compound I-89
M9 was used in place of M1 and benzo [ b ] phenanthrene [9,10-d ] thiophen-11-ylboronic acid was used in place of naphtho [2,3-b ] benzofuran-3-ylboronic acid, and the other raw materials and procedures were the same as in example 11, except that the appropriate material ratios were selected, whereby 65.1g of a pale yellow solid was obtained in a yield of about 83%.
Product MS (m/e): 784; elemental analysis (C)54H28N2OS2): theoretical value C: 82.63%, H: 3.60%, N: 3.57 percent; found value C: 82.83%, H: 3.78%, N: 3.77 percent.
Example 20
Figure BDA0002754186920000243
Synthesis of (Compound I-129)
The synthetic route is as follows:
Figure BDA0002754186920000244
the method comprises the following specific steps:
synthesis of Compound I-129
In a 1L three-necked flask, M10(33.3g, 0.1mol), naphtho [2,3-b ] was added]Benzofuran-3-ylboronic acid (26.2g, 0.1mol), sodium carbonate (21.2g, 0.2mol), toluene (150 mL), ethanol (150 mL), and water (150 mL), and Pd (PPh) was added after the reaction system was replaced with nitrogen gas for protection3)4(11.5g, 0.01 mol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. Reducing and distilling off the solvent, extracting by dichloromethane, drying by anhydrous magnesium sulfate, filtering, carrying out petroleum ether/ethyl acetate (2:1) column chromatography, carrying out rotary drying on the solvent, pulping by ethyl acetate, and filtering to obtain 40.0g of light yellow solid I-129-1 with the yield of about 85%;
A1L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, I-129-1(47.1g, 0.1mol), benzo [ b ] naphtho [1,2-d ] thiophen-10-ylboronic acid (27.8g, 0.1mol), cesium carbonate (39g, 0.12mol) and 400ml dioxane were added in this order, followed by stirring. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 52.1g pale yellow solid I-129 with yield about 78%.
Product MS (m/e): 668; elemental analysis (C)46H24N2O2S): theoretical value C: 82.62%, H: 3.62%, N: 4.19 percent; found value C: 82.82%, H: 3.42%, N: 4.38 percent.
According to the technical schemes of the examples 11 to 20, other compounds of I-1 to I-130 can be synthesized only by simply replacing corresponding raw materials and not changing any substantial operation.
Device examples the compounds of the invention were used as green host materials
The embodiment provides a group of OLED green light devices, and the structure of the device is as follows:
ITO/HATCN (1nm)/HT01(40nm)/NPB (20nm)/EML (30nm) (containing I-9)/Bphen (40nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
Figure BDA0002754186920000251
the preparation method comprises the following steps:
(1) the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent (volume ratio is 1: 1), baking in a clean environment until water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm; then evaporating a hole transport layer at the evaporation rate of 0.1nm/s and the evaporation film thickness of 20 nm;
(3) EML is vacuum evaporated on the hole transport layer to serve as a light emitting layer of the device, the EML comprises the main material I-9 and the dye material, the evaporation rate of the main material is adjusted to be 0.1nm/s by a multi-source co-evaporation method, and the dye material Ir (ppy)3The concentration of (2) is 5%, the total film thickness of evaporation plating is 30nm, and CBP is used as a contrast material of a main body material;
(4) taking Bphen as an electron transport layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40 nm;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
According to the same steps as the above, only replacing I-9 in the step (3) with I-13, I-20, I-29, I-32, I-47, I-58, I-68, I-89 and I-129 respectively to obtain the OLED-2 to OLED-10 provided by the invention.
Following the same procedure as above, only replacing I-9 in step (3) with CBP (comparative compound), comparative example OLED-11 provided by the present invention was obtained. The structure of the CBP is specifically as follows:
Figure BDA0002754186920000261
the performance of the obtained devices OLED-1 to OLED-11 is detected, and the detection results are shown in Table 1.
Table 1: performance test result of OLED device
Figure BDA0002754186920000262
Figure BDA0002754186920000271
From the above, the devices OLED-1 to OLED-10 prepared by using the organic material shown in formula I provided by the invention have higher current efficiency, and under the condition of the same brightness, the working voltage is obviously lower than that of the device OLED-11 using CBP as the main material, so that the organic material is a green light main material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. A polyheterocyclic compound having a structure according to formula I:
Figure FDA0002754186910000011
in the general formula (I), R1～R8At least one group in the aromatic group is an aromatic group containing a five-membered heterocycle, and the aromatic group containing the five-membered heterocycle is connected with a mother nucleus shown in a general formula (I) through a C atom; the remaining groups each independently represent a hydrogen atom, a halogen, a linear or branched alkyl group, a cycloalkyl group, an amino group, an alkylamino group, a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring.
2. Polyheterocycle compound according to claim 1, wherein the substituted or unsubstituted aromatic group containing a five-membered heterocycle contains at least one five-membered heterocycle, preferably one, two or three five-membered heterocycles; the five-membered heterocyclic ring contains at least one heteroatom, preferably one, two or three heteroatoms; the heteroatom is optionally selected from the group consisting of N atoms, S atoms, and O atoms; when the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains a plurality of hetero atoms, the respective hetero atoms may be the same as each other, may be partially the same as each other, or may be different from each other.
3. The polyheterocycle compound according to claim 1 or 2 wherein the substituted or unsubstituted five-membered heterocycle containing aromatic group is selected from the group consisting of: substituted or unsubstituted carbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl.
4. A polyheterocycle compound according to any one of claims 1 to 3 wherein in said substituted aromatic group containing a five-membered heterocycle, the substituents may be selected from the group consisting of: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, indolo, benzothieno, benzofuro; the number of the substituents is selected from 1 to 5, preferably an integer of 1 to 3.
5. The polyheterocyclic compound according to any one of claims 1 to 4 wherein the substituted or unsubstituted five-membered heterocycle containing aromatic group is selected from the group consisting of:
Figure FDA0002754186910000012
Figure FDA0002754186910000021
Figure FDA0002754186910000031
preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure FDA0002754186910000032
Figure FDA0002754186910000041
further preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from the group consisting of:
Figure FDA0002754186910000042
Figure FDA0002754186910000051
6. the polyheterocyclic compound according to any one of claims 1 to 5, wherein the compound is selected from the group consisting of compounds represented by the following general formulae I-1 to I-130:
Figure FDA0002754186910000052
Figure FDA0002754186910000061
Figure FDA0002754186910000071
Figure FDA0002754186910000081
Figure FDA0002754186910000091
Figure FDA0002754186910000101
Figure FDA0002754186910000111
Figure FDA0002754186910000121
Figure FDA0002754186910000131
Figure FDA0002754186910000141
Figure FDA0002754186910000151
Figure FDA0002754186910000161
Figure FDA0002754186910000171
Figure FDA0002754186910000181
Figure FDA0002754186910000191
7. use of the polyheterocyclic compound of any one of claims 1 to 6 in an organic electroluminescent device;
preferably, the polyheterocyclic compound is used as a light-emitting host material of an electroluminescent layer in an organic electroluminescent device.
8. An organic electroluminescent device comprising an electroluminescent layer containing the polyheterocyclic compound according to any one of claims 1 to 6;
preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer containing the polyheterocyclic compound of any one of claims 1 to 6, an electron transport layer, an electron injection layer and a cathode layer in sequence from bottom to top; preferably, the thickness of the electroluminescent layer can be 10 to 50nm, preferably 20 to 40 nm.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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