CN114805379B - Organic material containing heterocycle and application thereof - Google Patents

Organic material containing heterocycle and application thereof Download PDF

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CN114805379B
CN114805379B CN202210611472.5A CN202210611472A CN114805379B CN 114805379 B CN114805379 B CN 114805379B CN 202210611472 A CN202210611472 A CN 202210611472A CN 114805379 B CN114805379 B CN 114805379B
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substituted
organic material
electron withdrawing
unsubstituted aromatic
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CN114805379A (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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    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract

The invention relates to the technical field of organic electroluminescent display, in particular to an organic material containing heterocycle, and also discloses application of the organic material in an organic electroluminescent device. The heterocyclic organic material 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 heterocycle and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to a novel organic material containing heterocycle, 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 an electron transport material of an organic electroluminescent device, which is applied to an OLED device and has the advantages of low driving voltage and high luminous efficiency.
Specifically, in a first aspect, the present invention provides a heterocyclic ring-containing organic material having a structure as shown in 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 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 represents H, deuterium atom, halogen atom, straight-chain or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, R 1 ～R 4 At least one of which is a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties, and is linked to a parent nucleus represented by the general formula (I) through a C atom on the group.
As a preferred embodiment of the present invention, the R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from H or deuterium atoms.
Preferably, said R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing properties, the remainder being selected from H.
Preferably, said R 1 ～R 4 Two or more of them represent substitutionOr unsubstituted aromatic groups containing heteroatoms and having electron withdrawing properties, the groups represented are 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 ，R X1 Is phenyl.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a hetero atom and having an electron withdrawing property is a group containing at least one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, 1, 10-phenanthroline, pyridazinyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, s-triazinyl, quinolinyl, isoquinolinyl;
the phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, 1, 10-phenanthroline, pyridazinyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, s-triazinyl, quinolinyl, isoquinolinyl may further have a substituent selected from the group consisting of alkyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphto, benzimidazolyl, naphthyl, pyridyl, pyridoyl, pyrrolyl, pyrrolo, imidazolyl, pyrazolyl, pyrazolo, diazinyl, diazinoyl, 1, 10-phenanthroline, s-triazinyl, fluorenyl, oxyfluorenyl, thiofluorenyl, quinolinyl, isoquinolinyl, carbazolyl;
the hydrogen on the substituent may be further substituted with 1 or more of any of the following groups, respectively: alkyl, phenyl, deuterated phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, and dibenzothiophenyl.
As a preferred embodiment of the present invention, the R 1 ～R 4 Wherein one of them represents a substituted or unsubstituted aromatic group having a heteroatom and having electron withdrawing properties, and the remaining groups are H; or,
the R is 1 ～R 4 Two of them represent substituted or unsubstituted aromatic groups containing hetero atoms and having electron withdrawing properties, and the remaining groups are H.
As a preferred embodiment of the invention, the substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties 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 represented by the general formula (I) is selected from compounds represented by the following structural formula:
in a second aspect, the invention provides the use of said organic material in the manufacture of an organic electroluminescent device.
Preferably, the organic material is used as an electron transport material in an organic electroluminescent device.
In a third aspect, the invention provides an organic electroluminescent device, which comprises an electron transport layer, wherein the electron transport layer contains the heterocyclic organic material shown in the general formula (I).
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 device comprising the organic electroluminescent device according to the present invention.
In a fifth aspect, the present invention provides a lighting device comprising the organic electroluminescent device according to the present invention.
The invention provides a novel organic material containing a heterocyclic structure, which is specifically shown as a general formula (I), wherein a parent nucleus of the series of compounds has good thermal stability, and the structure has proper HOMO and LUMO energy levels and Eg; the electron-withdrawing group is connected with the organic light-emitting diode, so that the electron injection capability can be effectively enhanced, the electron transmission performance can be improved, the organic light-emitting diode can be well applied to OLED devices, the organic light-emitting diode can be used as an electron transmission material, and the photoelectric performance of the devices can be effectively improved.
The organic material containing the heterocyclic structure provided by the invention can be used as an electron transmission material, has higher electron transmission performance, better film stability and proper molecular energy level, can be applied to the field of organic electroluminescence, and can effectively improve the photoelectric performance of a device. Meanwhile, the Organic Light Emitting Diode (OLED) has the advantages of good thermal stability, stability and high efficiency, and can be well applied to OLED devices. Therefore, the driving voltage can be reduced, the luminous efficiency of the device is improved, and the device has important practical application value. The organic electroluminescent device made of the organic material has the characteristics of low driving voltage and high luminous efficiency. The device can be applied in the fields of display and 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) At the position ofInto 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:
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), (4-phenylquinazolin-2-yl) boric acid (25.0 g,0.1 mol), sodium carbonate (15.9 g,0.15 mol), toluene (150 mL), ethanol (150 mL) and water (150 mL) were added, and the reaction system was replaced with nitrogen and then 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), spin-dried, slurried with ethyl acetate, and filtered to give 37.2g of white solid I-1.
Product MS (m/e): 576.6; elemental analysis (C) 41 H 24 N 2 O 2 ): theoretical value C,85.40; h,4.20; n,4.86; o,5.55; measured value C:85.38, h:4.42, n:4.84.
EXAMPLE 2 Synthesis of Compound I-51
The synthetic route is as follows:
the synthesis process is as follows: A1L three-necked flask was stirred magnetically, and M3-3 (42.3 g,0.1 mol), 1, 3-benzothiazole-2-boronic acid (17.9 g,0.1 mol), cesium carbonate (39 g,0.12 mol) and 400ml of dioxane 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, and the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried to give 33.1g of white solid I-51.
Product MS (m/e): 521.6; elemental analysis (C) 34 H 19 NOS 2 ): theoretical value C,78.28; h,3.67; n,2.69; o,3.07; s,12.29; measured value C:78.27, H:3.51, N:2.68.
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), (4-phenylquinazolin-2-yl) boric acid (25.0 g,0.1 mol), sodium carbonate (15.9 g,0.15 mol), toluene (150 mL), ethanol (150 mL) and water (150 mL) were charged, and the reaction system was replaced with nitrogen and then 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. Evaporating off the solvent, extracting with dichloromethane, drying with anhydrous magnesium sulfate, filtering, subjecting to petroleum ether/ethyl acetate (2:1) column chromatography, and spin-dryingThe solvent, ethyl acetate, was slurried and filtered to give 47.5g of white solid I-73-1.
Product MS (m/e): 627.2; elemental analysis (C) 41 H 23 ClN 2 OS): theoretical value C,78.52; h,3.70; cl,5.65; n,4.47; o,2.55; s,5.11; measured value C:78.51, h:3.62, N,4.45.
A1L three-necked flask was stirred magnetically, and after nitrogen substitution, I-73-1 (62.7 g,0.1 mol), (2, 4-diphenylquinazolin-6-yl) boric acid (32.6 g,0.1 mol), cesium carbonate (39 g,0.12 mol) and dioxane 400ml 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 to give 54.4g of white solid I-73.
Product MS (m/e): 873.1; elemental analysis (C) 61 H 36 N 4 OS): theoretical value C,83.92; h,4.16; n,6.42; o,1.83; s,3.67; measured value C:83.91, h:3.92, n:6.43.
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 19
The embodiment provides a group of OLED blue light devices, and the device structure is as follows:
ITO/HATCN (10 nm)/HT (40 nm)/EML (30 nm)/any of the compounds (40 nm)/LiF (1 nm)/Al provided in examples 1-18, prepared by:
(1) Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in a mixed solvent of acetone and ethanol (volume ratio is 1:1), baking in a clean environment until the moisture is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with 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; wherein the structural formulas of HATCN and HT are as follows:
(3) Vacuum evaporating EML on the hole transmission layer as a light-emitting layer of the device, wherein the EML comprises a main material and a dye material, the evaporation rate of the main material ADN is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the concentration of the dye material BD01 is 5%, and the total evaporation film thickness is 30nm; the structural formulas of ADN and BD01 are as follows:
(4) Vacuum evaporating an electron transport layer material of the device on the light emitting layer, evaporating any one of the compounds provided in examples 1 to 18 as the electron transport material of the electron transport layer of the device at an evaporation rate of 0.1nm/s and an evaporation total film thickness of 40nm;
(5) Sequentially 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 an Al layer on the electron injection layer to serve as a cathode of the device, wherein the film thickness of the evaporated film is 150nm; the OLED-1 to OLED-18 devices provided by the invention are respectively obtained.
According to the same procedure as above, only the electron-transporting material in step (4) was replaced with the comparative compound C1, the structural formula was as follows, to obtain a comparative example device OLED-19.
Comparative compound C1.
The performance of the devices OLED-1 to OLED-19 obtained by the method is detected, and the detection results are shown in Table 3.
TABLE 3 Table 3
The results in Table 3 show that the novel organic material is used in organic electroluminescent device, and the produced device has high current efficiency, and the working voltage is obviously superior to that of the comparative device under the same current density, and the material has long service life and 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 (12)

1. An organic material containing a heterocycle, 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 X, Y may or may not be the sameSimultaneously;
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 represents H, deuterium atom, halogen atom, straight-chain or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, R 1 ～R 4 At least one of which is a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties and is linked to a parent nucleus represented by the general formula (I) through a C atom on the group;
the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing properties is a group containing at least one of a quinazolinyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, a pyridyl group, a 1, 10-phenanthroline group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a benzopyrazinyl group, a s-triazinyl group, a quinolyl group and an isoquinolyl group.
2. The organic material of claim 1, wherein R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from H or deuterium atoms.
3. The organic material of claim 2, wherein R 1 ～R 4 The term "medium" represents substituted or unsubstitutedSubstituted aromatic groups containing heteroatoms and having electron withdrawing properties, the remaining groups being selected from H;
the R is 1 ～R 4 When two or more of them represent substituted or unsubstituted aromatic groups having hetero atoms and having electron withdrawing properties, the groups represented are the same or different.
4. The organic material of claim 1 or 2, wherein the X, Y is each independently selected from O, S, NR X1 ，R X1 Is phenyl.
5. The organic material according to claim 1 or 2, wherein the quinazolinyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, 1, 10-phenanthroline, pyridazinyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, s-triazinyl, quinolinyl, isoquinolinyl may further have a substituent selected from the group consisting of alkyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphto, benzimidazolyl, naphthyl, pyridyl, pyridoyl, pyrrolyl, pyrrolo, imidazolyl, imidazo, pyrazolyl, pyrazolo, diazinyl, diazinoyl, 1, 10-phenanthroline, symtriazinyl, fluorenyl, dibenzofuranyl, thioquinolinyl, isoquinolinyl, carbazolyl;
the hydrogen on the substituent may be further substituted with 1 or more of any of the following groups, respectively: alkyl, phenyl, deuterated phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, and dibenzothiophenyl.
6. The organic material according to claim 1 or 2, wherein R 1 ～R 4 Wherein one of them represents a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing propertiesThe remaining groups are H; or,
the R is 1 ～R 4 Two of them represent substituted or unsubstituted aromatic groups containing hetero atoms and having electron withdrawing properties, and the remaining groups are H.
7. The organic material according to claim 1 or 2, wherein the substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties is selected from the group consisting of:
wherein "- -" in each substituent group represents a substitution position.
8. The organic material of claim 1, wherein the organic material is selected from the group consisting of compounds of the following structural formula:
9. use of an organic material according to any one of claims 1 to 8 for the preparation of an organic electroluminescent device.
10. The use according to claim 9, wherein the organic material is used as an electron transport material in an organic electroluminescent device.
11. An organic electroluminescent device, characterized in that it comprises an electron transport layer containing the organic material according to any one of claims 1 to 8.
12. A display device or a lighting device comprising the organic electroluminescent device as claimed in claim 11.
CN202210611472.5A 2022-05-31 2022-05-31 Organic material containing heterocycle and application thereof Active CN114805379B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150070928A (en) * 2013-12-17 2015-06-25 에스에프씨 주식회사 An electroluminescent compound and an electroluminescent device comprising the same
KR20150111106A (en) * 2014-03-25 2015-10-05 에스에프씨 주식회사 An organoelectro luminescent compounds and organoelectro luminescent device using the same
CN113196511A (en) * 2018-12-14 2021-07-30 三星显示有限公司 Organic electroluminescent device and spiro compound for organic electroluminescent device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150070928A (en) * 2013-12-17 2015-06-25 에스에프씨 주식회사 An electroluminescent compound and an electroluminescent device comprising the same
KR20150111106A (en) * 2014-03-25 2015-10-05 에스에프씨 주식회사 An organoelectro luminescent compounds and organoelectro luminescent device using the same
CN113196511A (en) * 2018-12-14 2021-07-30 三星显示有限公司 Organic electroluminescent device and spiro compound for organic electroluminescent device

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