CN114805381B - Organic material containing heterocyclic structure and application thereof - Google Patents

Organic material containing heterocyclic structure and application thereof Download PDF

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CN114805381B
CN114805381B CN202210611477.8A CN202210611477A CN114805381B CN 114805381 B CN114805381 B CN 114805381B CN 202210611477 A CN202210611477 A CN 202210611477A CN 114805381 B CN114805381 B CN 114805381B
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substituted
unsubstituted
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aromatic hydrocarbon
organic material
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CN114805381A (en
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郭宇星
李小赢
程丹丹
呼建军
曹占广
张朝霞
杭德余
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Beijing Yunji Technology Co Ltd
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Abstract

The invention relates to the technical field of organic electroluminescent display, in particular to an organic material containing a heterocyclic structure, and also discloses application of the organic material in an organic electroluminescent device. The organic material containing the heterocyclic structure provided by the invention is shown in the general formula (I), can be applied to the field of organic electroluminescence, and can be used as an electron transport material. The structural compound provided by the invention is applied to an OLED device, can reduce the driving voltage and improve the luminous efficiency of the device.

Description

Organic material containing heterocyclic structure and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to a novel organic material containing a heterocyclic structure, and also relates to application of the novel organic material in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements on the performance of flat panel display devices are increasing. Currently the main display technologies are plasma display devices, field emission display devices and organic electroluminescent display devices (OLEDs). Compared with a liquid crystal display device, the OLEDs do not need a backlight source, have wider visual angles and low power consumption, and have response speed which is 1000 times that of the liquid crystal display device, so that the OLEDs have wider application prospect.
Since the first report of high efficiency Organic Light Emitting Diodes (OLEDs), many scholars have been devoted to research how to improve the performance of OLED devices. The organic electron transport material is an important material for OLED devices. The organic charge transport material is an organic semiconductor material which can realize controllable directional and orderly movement of carriers under the action of an electric field when carriers (electrons or holes) are injected, thereby carrying out charge transport. The organic charge transport material is mainly transported holes, called hole type transport material, mainly transported electrons, called electron type transport material, or simply electron transport material. Organic charge transport materials have been developed to date, wherein hole transport materials are more various and have better properties, while electron transport materials are less various and have poorer properties. For example, the electron transport material Alq3 commonly used at present has high working voltage and serious power consumption due to low electron mobility; some electron transport materials such as LG201 have low triplet energy levels, and when phosphorescent materials are used as the light-emitting layer, an exciton blocking layer needs to be added, otherwise efficiency is lowered; still other materials, such as Bphen, crystallize easily, resulting in reduced lifetime. These problems with electron transport materials are all bottlenecks that affect the development of organic electroluminescent display devices. Therefore, the development of new electron transport materials with better performance would have important practical application value.
Disclosure of Invention
The invention aims to develop a novel electron transport material of an organic electroluminescent device, which is applied to an OLED device, can reduce driving voltage and improve luminous efficiency of the device.
Specifically, in a first aspect, the invention provides an organic material containing a heterocyclic structure, which has a structure shown as a general formula (I):
wherein X, Y are each independently selected from O, S, se, NR X1 、CR X2 R X3 、PR X4 And SiR X5 R X6 The X, Y may be the same or different;
R X1 、R X2 、R X3 、R X4 、R X5 and R is X6 Each independently selected from H, deuterium, halogen, substituted or unsubstituted alkyl, alkoxy or heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, alkylsilyl, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, aryl, aryloxy, heteroaryl, heteroaryloxy, arylsilyl, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, sulfanyl, sulfinyl, sulfonyl, phosphino;
R 1 ～R 4 each independently selected from H, deuterium, halogen, straight or branched alkyl, cycloalkyl, substituted or unsubstituted C 6 ～C 40 A monocyclic or polycyclic aromatic hydrocarbon group, and R 1 ～R 4 At least one of which is substituted or unsubstituted C 6 ～C 40 A monocyclic or polycyclic aromatic hydrocarbon group; r is R 1 ～R 4 May be the same or different.
The halogen atom is F, cl, br or I.
Straight chain alkyl means a compound of the formula C n H 2n+1 Linear alkyl groups including, but not limited to, methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. Preferably n is a linear alkyl group of 1 to 5.
Branched alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like. Branched alkyl groups having 1 to 5 carbon atoms are preferable.
Cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Cycloalkyl groups having 3 to 6 carbon atoms are preferable.
As a preferred embodiment of the present invention, the substituted or unsubstituted C 6 ～C 40 Wherein the monocyclic aromatic hydrocarbon group is an aromatic hydrocarbon group containing one benzene ring, and the polycyclic aromatic hydrocarbon group is a multi-benzene aliphatic hydrocarbon group, a biphenyl and biphenyl type polycyclic aromatic hydrocarbon group, a spirobifluorene group or a condensed ring aromatic hydrocarbon group.
Polycyclic aromatic hydrocarbon groups include, but are not limited to, groups comprising biphenyl, terphenyl, naphthalene, acenaphthene, fluorene, spirobifluorene, phenanthrene, pyrene, fluoranthene, chrysene, benzo (a) anthracene, benzofluoranthene, triphenylene, benzopyrene, perylene, indenofluorene.
Preferably, the substituted or unsubstituted C 6 ～C 40 The polycyclic aromatic hydrocarbon in the monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon is any one of a polyphenyl aliphatic hydrocarbon, a biphenyl polycyclic aromatic hydrocarbon, a spirobifluorene group and a condensed ring aromatic hydrocarbon, wherein the substituent is arbitrarily selected from the following groups: halogen, straight-chain or branched-chain alkyl, cycloalkyl, polycyclic aryl, polycyclic arylo, monocyclic aryl, monocyclic arylo, heterocyclic aryl, heterocyclic arylo, the number of the substituents being selected from integers from 1 to 7.
Further preferably, the substituted or unsubstituted C 6 ～C 40 Is selected from the group consisting of monocyclic aromatic hydrocarbon groups and polycyclic aromatic hydrocarbon groups: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzo (a) anthryl group, a substituted or unsubstituted benzo (b) fluoranthenyl group, a substituted or unsubstituted benzo (k) fluoranthenyl group, a substituted or unsubstituted benzo (a) pyrenyl group, a substituted or unsubstituted indenofluorenyl group;
the number of substituted substituents may be 1 to 3, said substituents being optionally selected fromHalogen, C 1-5 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, monocyclic aryl, monocyclic arylo, polycyclic aryl, polycyclic arylo; the hydrogen on the substituent may be further substituted with 1 to 2 of any substituent, respectively: c (C) 1-5 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, phenyl.
As a further preferred embodiment of the present invention, the substituted or unsubstituted C 6 ～C 40 Any of the monocyclic or polycyclic aromatic hydrocarbon groups selected from: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted indenofluorenyl group, a substituted or unsubstituted perylene group; the number of substituted substituents may be 1 to 3, said substituents being optionally selected from halogen, C 1-5 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, phenyl, biphenyl, naphthyl, naphthoyl, phenanthryl, benzo, triphenylene, fluoranthenyl; the hydrogen on the substituent may be further substituted with 1 to 2 of any substituent, respectively: c (C) 1-5 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, phenyl.
As a more preferred embodiment of the present invention, the substituted or unsubstituted C 6 ～C 40 Any of the monocyclic or polycyclic aromatic hydrocarbon groups selected from: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted indenofluorenyl group, a substituted or unsubstituted perylene group; the number of substituted substituents may be 1-2, said substituents being optionally selected from C 1-5 Straight-chain or branched alkyl, C 3-6 Cycloalkyl, phenyl, biphenyl, naphthyl, phenanthryl, benzo, triphenylene, naphtho, fluoranthenyl.
As a preferred embodiment of the present invention, the R 1 ～R 4 The term "medium" represents substituted or unsubstituted C 6 ～C 40 Except for the monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group, the rest is H or deuterium.
Preferably, said R 1 ～R 4 One or both of which represent substituted or unsubstituted C 6 ～C 40 A monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, and the balance thereof is H. When said R is 1 ～R 4 Two of (a) represent substituted or unsubstituted C 6 ～C 40 R in the case of monocyclic or polycyclic aromatic hydrocarbon groups 1 ～R 4 The same or different.
As a preferred embodiment of the present invention, in formula (I), each of said X, Y is independently selected from O, S, NR X1 The method comprises the steps of carrying out a first treatment on the surface of the The R is X1 Is phenyl.
As a preferred embodiment of the present invention, the substituted or unsubstituted C 6 ～C 40 Is selected from the group consisting of:
wherein "- -" in each substituent group represents a substitution position.
As a preferred embodiment of the present invention, the organic material containing a heterocyclic structure represented by the general formula (I) is selected from compounds represented by the following structural formula:
in a second aspect, the invention provides an application of the organic material containing the heterocyclic structure in preparing an organic electroluminescent device.
Preferably, the organic material containing a heterocyclic structure is used as an electron transport material in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device, which includes an electron transport layer, wherein the electron transport layer contains the organic material containing a heterocyclic structure.
As a preferred embodiment, the thickness of the electron transport layer may be 10 to 50nm, preferably 30 to 50nm.
In a fourth aspect, the present invention provides a display apparatus comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting device comprising the organic electroluminescent device.
The invention provides a novel organic material containing a heterocyclic structure, which is specifically shown as a general formula (I), and the mother nucleus structure containing the heterocyclic structure has stronger electron withdrawing capability and good thermal stability. The compounds of this structure have suitable HOMO and LUMO energy levels and Eg. Further, by introducing neutral groups into the parent nucleus structure, the electron transmission performance of the material can be further improved by changing the stacking mode among molecules.
The novel OLED material provided by the invention takes the heterocyclic structure as a parent nucleus, the parent nucleus structure has stronger electron-withdrawing capability, and a novel OLED material is obtained by introducing neutral groups into the parent structure. The material has higher electron transmission performance, better film stability and proper molecular energy level, can be applied to the field of organic electroluminescence, is used as an electron transmission material of an OLED device, is a stable and efficient electron transmission material, can effectively reduce the driving voltage of the device, improves the luminous efficiency of the device and improves the photoelectric performance of the device. The novel OLED material provided by the invention can be well applied to OLED devices, and the devices have the characteristics of low driving voltage and high luminous efficiency, and have important practical application values. The device can be applied in the fields of display and illumination.
Through experiments, the compound disclosed by the invention is applied to an OLED device and used as an electron transmission material, so that the driving voltage can be reduced, the luminous efficiency of the device can be improved, the service life of the device can be prolonged, the photoelectric property of the device can be effectively improved, and the manufactured OLED device can be applied to the field of display or illumination.
Detailed Description
The technical scheme of the invention is described in detail through specific examples. The following examples are given to illustrate the present invention but are not to be construed as limiting the scope of the invention, and all equivalent changes or modifications that may be made without departing from the spirit of the invention as disclosed herein are intended to be included within the scope of the appended claims.
According to the preparation method provided by the invention, the preparation method can be realized by adopting known common means by a person skilled in the art, such as further selecting a proper catalyst and a proper solvent, determining a proper reaction temperature, a proper time, a proper material ratio and the like, and the invention is not particularly limited. Unless otherwise indicated, starting materials for solvents, catalysts, bases, etc. used in the preparation process may be synthesized by published commercial routes or by methods known in the art.
By adopting the preparation method provided by the invention, a series of compounds shown in the general formula (I) are prepared.
Synthetic intermediates
Synthesis of intermediate M1-1
The synthetic route is as follows:
the specific operation steps are as follows:
(1) Into a 2L three-necked flask, 2-bromobenzofuran (19.7 g,0.1 mol), methyl 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate (26.2 g,0.1 mol), sodium carbonate (26.5 g,0.25 mol), toluene 200mL, ethanol 200mL, and water 150mL were added, and after the reaction system was purged with nitrogen, pd (PPh) 3 ) 4 (11.5 g,10 mmol). The reaction was heated at reflux for 6 hours and stopped. Adding water into the system, standing for separating liquid, drying the organic phase by anhydrous magnesium sulfate, evaporating the solvent, extracting by ethyl acetate, drying by anhydrous magnesium sulfate, filtering, purifying by column chromatography to obtain 21.7g of white solid M1-1a, wherein the yield is about 86%.
(2) Into a 1L three-necked flask, M1-1a (25.2 g,0.1 mol), sodium hydroxide (0.8 g,0.2 mol), 200mL of ethanol, and the reaction was refluxed for 2 hours to stop the reaction. The pH is regulated to 2-3 by 50% dilute hydrochloric acid, the mixture is stirred for half an hour, and the mixture is filtered by suction to obtain 23.3g of white solid M1-1b, and the yield is about 98%.
(3) Into a 1L three-necked flask, M1-1b (23.8 g,0.1 mol), 25g of methanesulfonic acid and 200mL of toluene were added, stirring and heating were started, the mixture was reacted at 90-100℃for 2 hours, cooled to room temperature, 200mL of distilled water was added, stirring was performed for half an hour, and suction filtration was performed to obtain 19.8g of a white solid M1-1c, the yield of which was about 90%.
(4) 4-bromo-1-iodo-2-phenoxybenzene (37.5 g,0.10 mol), anhydrous tetrahydrofuran, and liquid nitrogen were added to a dry 2L three-necked flask under nitrogen protection, and n-butyllithium (100 mL,0.25 mol) was slowly added dropwise after dropping, the dropping funnel was flushed with 50mL THF, and the flask was incubated and stirred for 1h after dropping. In a low temperature system at-78deg.C, 60mL of an anhydrous tetrahydrofuran solution of M1-1c (22.0 g,0.1 mol) was slowly added dropwise to a three-necked flask under nitrogen protection, then the dropping funnel was rinsed with a small amount of THF, then naturally warmed to room temperature, stirred for 10 hours, and the reaction was quenched with saturated sodium bicarbonate solution. The organic phase was separated, extracted, dried, column chromatographed, spin-dried to give 38.0g of product M1-1d in 81% yield.
(5) M1-1d (46.9 g,0.1 mol), 50mL of concentrated hydrochloric acid and 200mL of glacial acetic acid are added into a 1L three-necked flask, stirring and heating are started, reaction is carried out at 100 ℃ for 4 hours, and the temperature is reduced to room temperature. 200ml toluene and 100ml water are added, the mixture is kept stand for liquid separation, the organic phase is washed to be neutral, the organic phase is separated, extracted, dried, subjected to column chromatography and the solvent is spun-dried, and 38.3g of white solid M1-1 is obtained, and the yield is about 85%.
Product MS (m/e): 451.2; elemental analysis (C) 27 H 15 BrO 2 ): theoretical value: c,71.86; h,3.35; br,17.70; o,7.09, found: c:71.84, H:3.21.
with reference to the above synthetic methods of intermediates, other intermediate compounds required in the preparation of the compounds of the present invention may be prepared. When other intermediates are prepared, corresponding raw materials are replaced, proper material ratios are selected, the synthesis steps are the same as those of the intermediate M1-1, and similar intermediates can be obtained.
Specifically, the intermediate is synthesized according to the general formula, wherein, atoms represented by X and Y can be selected as N, O, S, NRx, and when X and Y are N, the substituent of N can be hydrogen or C 1 ～C 8 Alkyl, C of (2) 5 ～C 10 Cycloalkyl, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 3 ～C 30 One or a combination of heterocyclic aryl groups of (C), X and Y may be the same or different.
Synthesis of intermediate of general formulae M1-M7
The synthetic route of intermediate M1 is:
the synthetic route of the intermediate M2 is as follows:
the synthetic route of intermediate M3 is:
the synthetic route of intermediate M4 is:
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the synthetic route of intermediate M5 is:
the synthetic route of intermediate M6 is:
the synthetic route of intermediate M7 is:
according to the above method, the reaction raw materials were replaced correspondingly, and specific intermediates shown in the following table 1 were synthesized.
TABLE 1
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Other types of intermediates similar to the structure of the invention can be correspondingly replaced and synthesized by referring to the method, and the target intermediates can be obtained, and the description of the method is omitted.
The synthesis of specific target compounds was performed using the above intermediates synthesized according to the present invention.
EXAMPLE 1 Synthesis of Compound I-1
The synthetic route is as follows:
the synthesis process is as follows: into a 1L three-necked flask, M1-1 (45.1 g,0.1 mol), phenylboronic acid (12.2, 0.1 mol), sodium carbonate (15.9 g,0.15 mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and the reaction system was followedPd (PPh) was added after the protection by nitrogen substitution 3 ) 4 (11.5 g,10 mmol). The reaction was heated to reflux (the temperature in the system was 70 to 80 ℃) for 3 hours, and the reaction was stopped. The solvent was removed by evaporation, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column chromatographed on petroleum ether/ethyl acetate (2:1), spin-dried, slurried with ethyl acetate, and filtered to give 27.5g of white solid I-1.
Product MS (m/e): 448.5; elemental analysis (C) 33 H 20 O 2 ): theoretical value C,88.37; h,4.49; o,7.13; measured value C:88.36, H:4.21.
EXAMPLE 2 Synthesis of Compound I-56
The synthetic route is as follows:
the synthesis process is as follows: A1L three-necked flask was stirred magnetically, and M3-8 (42.3 g,0.1 mol), (3, 4-dimethylphenyl) boric acid (15.0 g,0.1 mol), cesium carbonate (39 g,0.12 mol) and dioxane 400ml were sequentially added after nitrogen substitution, followed by stirring. After a further nitrogen displacement (0.8 g,4 mmol) tri-tert-butylphosphine and (1.4 g,1.5 mmol) 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 reducing the temperature after the reaction is finished. The mixture was neutralized, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried to give 29.5g of white solid I-56.
Product MS (m/e): 492.6; elemental analysis (C) 35 H 24 OS): theoretical value C,85.33; h,4.91; o,3.25; s,6.51; measured value C:85.31, h:4.75.
EXAMPLE 3 Synthesis of Compound I-73
The synthetic route is as follows:
the synthesis process is as follows: into a 1L three-necked flask, M4-1 (50.2 g,0.1 mol), anthracene-2-yl boronic acid (22.2 g,0.1 mol), sodium carbonate (15.9 g,0.15 mol), toluene 150mL, ethanol 150mL, and water 150mL were placed, and after the reaction system was purged with nitrogen, pd (PPh) 3 ) 4 (11.5 g,10 mmol). The reaction was heated to reflux (the temperature in the system was 70 to 80 ℃) for 3 hours, and the reaction was stopped. The solvent was removed by evaporation, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column chromatographed on petroleum ether/ethyl acetate (2:1), the solvent was dried by spinning, slurried with ethyl acetate, and filtered to give 43.5g of white solid I-73-1 in 72.6% yield.
Product MS (m/e): 599.1; elemental analysis (C) 41 H 23 ClOS): theoretical value C,82.19; h,3.87; cl,5.92; o,2.67; s,5.35; measured value C:82.18, h:3.65.
A1L three-necked flask was stirred magnetically, and after nitrogen substitution, I-73-1 (59.9 g,0.1 mol), anthracene-9-yl boronic acid (22.2 g,0.1 mol), cesium carbonate (39 g,0.12 mol) and dioxane (400 ml) were sequentially added, followed by stirring. After a further nitrogen displacement (0.8 g,4 mmol) tri-tert-butylphosphine and (1.4 g,1.5 mmol) 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 reducing the temperature after the reaction is finished. The mixture was neutralized, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried by spin-drying to give 44.2g of white solid I-73 in 59.6% yield.
Product MS (m/e): 740.9; elemental analysis (C) 55 H 32 OS): theoretical value C,89.16; h,4.35; o,2.16; s,4.33; measured value C:89.15, h:4.15.
EXAMPLE 4 Synthesis of Compound I-83
The synthetic route is as follows:
the synthesis process is as follows: into a 1L three-necked flask, M8-1 (54.6 g,0.1 mol), anthracene-2-yl boronic acid (44.4 g,0.2 mol), sodium carbonate (31.8 g,0.3 mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and after the reaction system was replaced with nitrogen gas and the mixture was protected, pd (PPh) 3 ) 4 (23 g,20 mmol). The reaction was heated to reflux (the temperature in the system was 70 to 80 ℃) for 5 hours, and the reaction was stopped. The solvent was removed by evaporation, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column chromatographed on petroleum ether/ethyl acetate (2:1), the solvent was dried by spinning, slurried with ethyl acetate, and filtered to give 46.2g of white solid I-83 in 62.4% yield.
Product MS (m/e): 740.9; elemental analysis (C) 55 H 32 OS): theoretical value C,89.16; h,4.35; o,2.16; s,4.33; measured value C:89.18, h:4.14.
with reference to the above method, specific compounds listed in the present invention were synthesized. Table 2 below shows examples of synthesis of some of the compounds.
TABLE 2
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Example 18
The embodiment provides a group of OLED red light devices, which have the following structure:
ITO/HATCN (10 nm)/HT (40 nm)/EB (5 nm)/EML (30 nm)/HB (10 nm)/any of the compounds (40 nm)/LiF (1 nm)/Al provided in examples 1-17, prepared by:
(1) Ultrasonically cleaning a glass substrate coated with an ITO transparent conductive film layer on the surface in a cleaning solution, ultrasonically treating in deionized water, ultrasonically degreasing in an acetone/ethanol mixed solvent (volume ratio is 1:1), baking in a clean environment until the moisture is completely removed, performing etching and ozone treatment by an ultraviolet lamp, and bombarding the surface by a low-energy cation beam;
(2) Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, vacuum evaporating HATCN as a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 10nm; evaporating a hole transport layer HT, wherein the evaporation rate is 0.1nm/s, and the thickness is 40nm; then evaporating an EB layer serving as an electron blocking layer on the hole transport layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 5nm; wherein HATCN, HT, EB has the following structural formula:
(3) Vacuum evaporating EML (electro-mechanical layer) on the electron blocking layer as a light-emitting layer of the device, wherein the EML comprises a main body material and a dye material, the main body material is PRH01, and the dopant, namely the dye material is Ir (piq), by utilizing a multi-source co-evaporation method 2 The acac, the evaporation rate of the main material is regulated to be 0.1nm/s, the concentration of the doping agent is 5%, and the total film thickness of evaporation is 30nm; wherein PRH01, ir (piq) 2 The structural formula of acac is as follows:
(4) Continuously evaporating HB with the thickness of 10nm to form a hole blocking layer, wherein the evaporation rate is 0.1nm/s; then, vacuum evaporation is carried out on the compound to form an electron transport layer with the film thickness of 40nm, any compound provided in the examples 1-17 is taken as an electron transport material of the electron transport layer of the device, vacuum evaporation is continuously carried out on the hole blocking layer, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 40nm, so that the electron transport layer is obtained; wherein HB has the following structural formula:
(5) Vacuum evaporating LiF with the thickness of 1nm on the electron transport layer to serve as an electron injection layer of the device, and continuously evaporating Al on the electron injection layer to serve as a cathode of the device, wherein the film thickness of the evaporated film is 150nm; the series of OLED-1 to OLED-17 devices provided by the invention are obtained.
According to the same procedure as above, only the electron-transporting material in step (4) was replaced with the following comparative compound C1, the structural formula of which is shown below, to obtain a comparative example device OLED-18.
Comparative compound C1.
The performance of the devices OLED-1 to OLED-18 obtained by the method is detected. The test results are shown in Table 3.
TABLE 3 Table 3
As can be seen from the data in table 3, the current efficiency of the devices OLED-1 to OLED-17 prepared by using the compounds provided by the present invention is higher, and the operating voltage is significantly lower than that of the device OLED-18 using the comparative compound Bphen as an electron transport material at the same current density, and the lifetime is longer. The result shows that the novel organic material is used for the organic electroluminescent device, can effectively reduce the driving voltage, improve the current efficiency, prolong the service life of the device and is an electron transport material with good performance.
While the invention has been described in detail in the foregoing general description, embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.

Claims (14)

1. An organic material containing a heterocyclic structure, characterized by having a structure represented by the general formula (I):
wherein X, Y are each independently selected from O, S, se, NR X1 、CR X2 R X3 、PR X4 And SiR X5 R X6 The X, Y may be the same or different;
R X1 、R X2 、R X3 、R X4 、R X5 and R is X6 Each independently selected from H, deuterium, halogen, substituted or unsubstituted alkyl, alkoxy or heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, alkylsilyl, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, aryl, aryloxy, heteroaryl, heteroaryloxy, arylsilyl, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, sulfanyl, sulfinyl, sulfonyl, phosphino;
R 1 ～R 4 each independently selected from H, deuterium, halogen, straight or branched alkyl, cycloalkyl, substituted or unsubstituted C 6 ～C 40 A monocyclic or polycyclic aromatic hydrocarbon group, and R 1 ～R 4 At least one of which is substituted or unsubstituted C 6 ～C 40 A monocyclic or polycyclic aromatic hydrocarbon group; r is R 1 ～R 4 May be the same or different;
the C is 6 ～C 40 The monocyclic or polycyclic aromatic hydrocarbon is aromatic hydrocarbon containing one benzene ring, polyphenyl aliphatic hydrocarbon, biphenyl and biphenyl polycyclic aromatic hydrocarbon, spirobifluorene group or condensed ring aromatic hydrocarbon, the C 6 ～C 40 The substituents of the monocyclic or polycyclic aromatic hydrocarbon groups are optionally selected from: halogen, straight-chain or branched alkyl, cycloalkyl,Polycyclic aryl, polycyclic arylo, monocyclic aryl, monocyclic arylo, heterocyclic aryl, heterocyclic arylo.
2. The organic material of claim 1, wherein the substituted or unsubstituted C 6 ～C 40 The number of substituents of the monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group is an integer of 1 to 7.
3. The organic material according to claim 1 or 2, wherein the substituted or unsubstituted C 6 ～C 40 Is selected from the group consisting of monocyclic aromatic hydrocarbon groups and polycyclic aromatic hydrocarbon groups: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzo (a) anthryl group, a substituted or unsubstituted benzo (b) fluoranthenyl group, a substituted or unsubstituted benzo (k) fluoranthenyl group, a substituted or unsubstituted benzo (a) pyrenyl group, a substituted or unsubstituted indenofluorenyl group; the number of substituted substituents may be 1 to 3, said substituents being optionally selected from halogen, C 1-5 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, monocyclic aryl, monocyclic arylo, polycyclic aryl, polycyclic arylo; the hydrogen on the substituent may be further substituted with 1 to 2 of any substituent, respectively: c (C) 1-5 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, phenyl.
4. The organic material according to claim 1 or 2, wherein R 1 ～R 4 The term "medium" represents substituted or unsubstituted C 6 ～C 40 Except for the monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group, the rest is H or deuterium.
5. The organic material according to claim 4, whereinWherein R is as follows 1 ～R 4 One or both of which represent substituted or unsubstituted C 6 ～C 40 A monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, and the balance thereof is H.
6. The organic material of claim 1 or 2, wherein the X, Y is each independently selected from O, S, NR X1 The method comprises the steps of carrying out a first treatment on the surface of the The R is X1 Is phenyl.
7. The organic material according to claim 1 or 2, wherein the substituted or unsubstituted C 6 ～C 40 Is selected from the group consisting of:
wherein "- -" in each substituent group represents a substitution position.
8. The organic material according to claim 1, wherein the organic material containing a heterocyclic structure is selected from compounds represented by the following structural formula:
9. use of an organic material containing a heterocyclic structure as described in any one of the claims 1-8 for the preparation of an organic electroluminescent device.
10. The use according to claim 9, wherein the organic material comprising a heterocyclic structure is used as an electron transport material in an organic electroluminescent device.
11. An organic electroluminescent device, comprising an electron transport layer, wherein the electron transport layer contains the organic material containing a heterocyclic structure according to any one of claims 1 to 8.
12. The organic electroluminescent device of claim 11, wherein the electron transport layer has a thickness of 10 to 50nm.
13. The organic electroluminescent device of claim 12, wherein the electron transport layer has a thickness of 30 to 50nm.
14. A display device or a lighting device comprising the organic electroluminescent device as claimed in any one of claims 11 to 13.
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KR20150111106A (en) * 2014-03-25 2015-10-05 에스에프씨 주식회사 An organoelectro luminescent compounds and organoelectro luminescent device using the same
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