CN104629731A - Organic compound and applications of organic compound in electroluminescent devices - Google Patents

Organic compound and applications of organic compound in electroluminescent devices Download PDF

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CN104629731A
CN104629731A CN201310554947.2A CN201310554947A CN104629731A CN 104629731 A CN104629731 A CN 104629731A CN 201310554947 A CN201310554947 A CN 201310554947A CN 104629731 A CN104629731 A CN 104629731A
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CN104629731B (en
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马晓宇
王辉
高春吉
赵贺
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The present invention relates to an organic electroluminescent material and a preparation method thereof, wherein the technical problem that the luminous efficiency of the existing luminescent material can not meet the requirement of OLED is solved with the present invention. According to the present invention, according to the organic electroluminescent material, the substituted thiazolyl group is connected to the o-phenanthroline group so as to exhibit the high electron mobility, the molecular stacking regularity can be increased through the symmetrical molecule structure so as to improve the current-carrying electron mobility to a certain extent and easily form the uniform non-crystalline film during the vacuum evaporation; and the compound has the high stability at a room temperature, and the device applying the compound further has the high stability.

Description

Organic compound and the application in electroluminescent device thereof
Technical field
The present invention relates to a kind of novel organic materials, and the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
As a rule, electron transport material all has the plane aromatics of large conjugated structure, they mostly have and connect nucleophobic ability preferably, under certain forward bias, effectively can transmit electronics again, electron transport material of good performance known is at present also few, and electron transport material available at present mainly contains oxine aluminium compounds simultaneously, furodiazole compound, quinoxaline compound, the polymkeric substance of nitrile group-containing, other nitrogen-containing heterocycle compound etc.
Therefore to design an electron transport material that organic electroluminescence device efficiency can be made significantly to promote, following character need be possessed: (1) has reversible electrochemical reduction and enough high also original units; (2) needing suitable HOMO and LUMO makes electronics have minimum injection energy gap, to reduce initial and operating voltage; (3) higher electronic mobility is needed; (4) glass transition temperature had and thermostability; (5) there is noncrystalline film.
Summary of the invention
The invention provides a kind of containing benzothiazolyl phenanthroline compounds.This compound structure is symmetrical, and preparation technology is simple, has higher luminous efficiency and high carrier mobility, can be used for the electron transfer layer of electroluminescent cell.The device applied significantly can reduce driving voltage, improves current efficiency.
Technical scheme of the present invention is as follows,
A kind of benzothiazolyl phenanthroline compounds, wherein, the general formula of molecular structure of described benzothiazolyl phenanthroline compounds is as shown in the formula (1):
................（1）
In general formula (1):
R 1, R 2and R 3independently selected from the aromatic group of general formula (2) or (3) 5 ~ 60 carbon atoms containing benzothiazole group.
..................（2）
.................（3）
Wherein, preferred R 4and R 5be selected from hydrogen atom, or be selected from the alkyl of carbon atom number from 1 ~ 6 and alkoxyl group.
More preferably R is worked as 1during for formula (2), R 4for nothing, R 5for hydrogen atom;
Work as R 1during for formula (3), R 4for nothing;
Work as R 1during for formula (2), R 4for nothing, R 5for phenyl;
Work as R 1during for formula (2), R 4for phenyl, R 5for nothing;
Work as R 2during for formula (2), R 4for nothing, R 5for hydrogen atom;
Work as R 2during for formula (3), R 4for nothing;
Work as R 2during for formula (2), R 4for nothing, R 5for phenyl;
Work as R 2during for formula (2), R 4for phenyl, R 5for nothing;
Work as R 3during for formula (2), R 4for nothing, R 5for hydrogen atom;
Work as R 3during for formula (3), R 4for nothing;
Work as R 3during for formula (2), R 4for nothing, R 5for phenyl;
Work as R 3during for formula (2), R 4for phenyl, R 5for nothing.
In order to compound of the present invention is described better, we illustrate the compound 001 ~ 012 of the preferred structure formula of general formula of the present invention (1), as follows:
Be more than the molecular structural formula of some particular compound, but benzothiazolyl phenanthroline class luminous organic material provided by the present invention is not limited to the compound shown in listed molecular structural formula, every R 1and R 2the benzothiazolyl phenanthroline class series compound that base replaces is included in benzothiazolyl phenanthroline class luminous organic material provided by the present invention.
Also provide the preparation method of described benzothiazolyl phenanthroline class luminous organic material in the present invention, concrete steps and the condition of this preparation method are as follows:
In molar ratio for 2:1 takes bromo benzothiazole amine phenanthroline and the boric acid containing R substituent, mol ratio is that 1:1.25:0.04 takes phenylo boric acid, salt of wormwood and tetrakis triphenylphosphine palladium, and solvent is toluene and water, described ratio is toluene: water is 2:1, be warmed up to 100 DEG C, react 20 hours, cooling, suction filtration, ethanol is washed, separatory, column chromatography, recrystallization, obtains benzothiazolyl phenanthroline compounds.
Beneficial effect of the present invention:
The benzothiazolyl phenanthroline compounds that the present invention prepares, from compound structure and character relation, the reduction potential of heterogeneous ring compound is lower than the pure aromatic series of analog structure, is conducive to accepting electronics, thus shows good electronic transport property.Phenanthroline analog derivative has good conjugate planes and lower HOMO energy level, and therefore the thiazolyl group of replacement is connected on phenanthroline base by we, can show high electron mobility; The regularity of molecular stacks can be increased with molecular configurational symmetry, also improve current-carrying electrons mobility to a certain extent.The nonplanarity of phenyl thiazole base, xenyl benzothiazolyl or naphthyl benzothiazolyl can make this compounds on space multistory, have distortion to a certain degree, formed when being more conducive to vacuum evaporation all and non-crystalline film.Compound of the present invention at room temperature has higher stability, and the device applied also has higher stability.
  
Embodiment
The present invention can be set forth in more detail by following examples, instead of wish that the present invention is limited therewith.
Compou nd synthesis embodiment:
Various pharmaceutical chemicalss used in the present invention are as phenanthroline, tert-butyl lithium, 1,3-benzothiazole ylboronic acid, 6-phenylbenzothiazol, 2-(4-bromophenyl) basic chemical industry such as benzothiazole, benzothiazole raw material all can Chemical market conveniently buy at home, and all the other several important intermediates can synthesize by following method:
1, aphthothiazoles ylboronic acid
Under nitrogen protection, aphthothiazoles (18.5,0.1mol) is dissolved in the dry tetrahydrofuran of 300mL through the process of Na/ benzophenone, cooled with liquid nitrogen, stirs lower successively slow dropping 40mL butyllithium (0.1mol, 2.5molL -1), after stirring 1.5h, drip NBS(0.11mol), after dripping, reaction 10min, slowly rises to room temperature reaction 2h, adopts NaHSO 3decolouring, product 200mL extracted with diethyl ether three times, merges organic phase, anhydrous MgSO 4drying, revolves and steams except desolventizing, and thick product, through column chromatography method purifying, obtains 2-bromine aphthothiazoles 19.2g product and drops into next step reaction.Under 1L nitrogen protection, previous step product (13.2g, 0.05mol) is dissolved in the dry tetrahydrofuran of 200mL through the process of Na/ benzophenone, cooled with liquid nitrogen, stirs lower successively slow dropping 20mL butyllithium (0.05mol, 2.5molL -1), three isopropoxy boric acid ester 30mL (0.243mol), after finishing, naturally stir and rise to room temperature.Add the hydrolysis of 200mL diluted hydrochloric acid aqueous solution, extraction into ethyl acetate, merge organic layer, revolve and steam except desolventizing, product drops into next step reaction.
2, the synthesis of 6,6-phenylbenzothiazol-2-boric acid
Under nitrogen protection, 6-phenylbenzothiazol (21.1g, 0.1mol) is dissolved in the dry tetrahydrofuran of 300mL through the process of Na/ benzophenone, cooled with liquid nitrogen, stirs lower successively slow dropping 40mL butyllithium (0.1mol, 2.5molL -1), after stirring 1.5h, drip NBS(0.11mol), after dripping, reaction 10min, slowly rises to room temperature reaction 2h, adopts NaHSO 3decolouring, product 200mL extracted with diethyl ether three times, merges organic phase, anhydrous MgSO 4drying, revolves and steams except desolventizing, and thick product, through column chromatography method purifying, obtains 2-bromo-6-phenylbenzothiazol 20.5g product and drops into next step reaction.Under nitrogen protection, previous step product (13.2g, 0.05mol) is dissolved in the dry tetrahydrofuran of 200mL through the process of Na/ benzophenone, cooled with liquid nitrogen, stirs lower successively slow dropping 20mL butyllithium (0.05mol, 2.5molL -1), three isopropoxy boric acid ester 30mL (0.243mol), after finishing, naturally stir and rise to room temperature.Add the hydrolysis of 200mL diluted hydrochloric acid aqueous solution, extraction into ethyl acetate, merge organic layer, revolve and steam except desolventizing, product drops into next step reaction.
3, the synthesis of 4,7-benzothiazolyl phenylo boric acids
Under nitrogen protection, by 2-(4-bromophenyl) benzothiazole (14.5g, 0.05mol) is dissolved in the dry tetrahydrofuran of 200mL through the process of Na/ benzophenone, cooled with liquid nitrogen, stirs successively slowly to drip 20mL butyllithium (0.05mol, 2.5molL down -1), three isopropoxy boric acid ester 30mL (0.243mol), after finishing, naturally stir and rise to room temperature.Add the hydrolysis of 200mL diluted hydrochloric acid aqueous solution, extraction into ethyl acetate, merge organic layer, revolve and steam except desolventizing, product drops into next step reaction.
The synthesis of embodiment 1 compound 001
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), 1,3-benzothiazole ylboronic acid (6.37g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain white crystalline solid 3.84g, productive rate 86%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 446.55; Test value is 446.55.Ultimate analysis: calculated value is C:69.93%; H:3.16%; N:12.55%; S:14.36%; Test value is C:69.92%; H:3.15%; N:12.56%; S:14.37%;
The synthesis of embodiment 2 compound 20 02
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), aphthothiazoles ylboronic acid (5.73g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 4.54g, productive rate 83%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 546.66; Test value is 546.66.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.70%; H:3.33%; N:10.25%; S:11.72%;
The synthesis of embodiment 3 compound 003
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), 6-phenylbenzothiazol ylboronic acid (6.38g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, and organic phase is washed three times also with after anhydrous Na 2SO4 drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5.09g, productive rate 85%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 598.74; Test value is 598.75.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.70%; H:3.34%; N:10.25%; S:11.71%;
The synthesis of embodiment 4 compound 004
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), 7,4-benzothiazolyl phenylo boric acid (6.38g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5.13g, productive rate 86%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 598.74; Test value is 598.73.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.31%; N:10.24%; S:11.74%;
The synthesis of embodiment 5 compound 005
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), 1,3-benzothiazole ylboronic acid (6.37g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain white crystalline solid 3.8g, productive rate 85%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 446.55; Test value is 446.57.Ultimate analysis: calculated value is C:69.93%; H:3.16%; N:12.55%; S:14.36%; Test value is C:69.93%; H:3.18%; N:12.53%; S:14.36%;
The synthesis of embodiment 6 compound 006
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), aphthothiazoles ylboronic acid (5.73g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 4.49g, productive rate 82%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 546.66; Test value is 546.65.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.33%; N:10.24%; S:11.72%;
The synthesis of embodiment 7 compound 007
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), 6-phenylbenzothiazol ylboronic acid (6.38g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain light yellow solid 5.03g, productive rate 84%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 598.74; Test value is 598.73.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.34%; N:10.23%; S:11.72%;
The synthesis of embodiment 8 compound 008
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), 7,4-benzothiazolyl phenylo boric acid (6.38g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain light pink solid 5g, productive rate 83.5%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 598.74; Test value is 598.74.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.31%; N:10.24%; S:11.74%;
The synthesis of embodiment 9 compound 009
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), 1,3-benzothiazole ylboronic acid (6.37g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain white crystalline solid 3.82g, productive rate 85.5%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 446.55; Test value is 446.55.Ultimate analysis: calculated value is C:69.93%; H:3.16%; N:12.55%; S:14.36%; Test value is C:69.92%; H:3.18%; N:12.54%; S:14.36%;
The synthesis of embodiment 10 compound 010
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), aphthothiazoles ylboronic acid (6.37g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 4.65g, productive rate 85%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 546.66; Test value is 546.65.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.34%; N:10.23%; S:11.72%;
The synthesis of embodiment 11 compound 011
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), 6-phenylbenzothiazol ylboronic acid (6.38g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5g, productive rate 83.5%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 598.74; Test value is 598.73.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.34%; N:10.23%; S:11.72%;
The synthesis of embodiment 12 compound 012
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), 4,7-benzothiazolyl phenylo boric acid (6.38g, 0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) be dissolved in the mixed solution of 75mL toluene and water, adding 50mL concentration of potassium carbonate is 2molL -1solution, cools after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three times and uses anhydrous Na 2sO 4after drying, through methylene dichloride/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5.03g, productive rate 84%, HPLC purity is greater than 99%.Mass spectrum: calculated value is 598.74; Test value is 598.73.Ultimate analysis: calculated value is C:74.70%; H:3.32%; N:10.25%; S:11.73%; Test value is C:74.71%; H:3.34%; N:10.23%; S:11.72%;
Here is the Application Example of the compounds of this invention:
Comparing embodiment 1: adopt compound of the present invention as the electron transport material in OLED, adopts current material Bphen as electron transport material, device architecture ITO/NPB (40nm)/Ir (ppy) 3(10wt%) (30nm)/Bphen (20nm)/
LiF(0.5nm)/Al(150nm)。
Device fabrication process is as follows: will be coated with sheet glass supersound process in commercial detergent of ITO transparency conducting layer, rinse in deionized water, ultrasonic oil removing in acetone, alcohol mixed solvent, be baked under clean environment and remove moisture content completely, rinse with UV-light and ozone, and with low energy positively charged ion bundle bombarded surface.
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10 -5~ 9 × 10 -3pa, on above-mentioned anode tunic, vacuum evaporation NPB is as hole transmission layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm: vacuum evaporation Ir (ppy) on hole transmission layer 3(10wt%) as the luminescent layer of device, evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm; On luminescent layer, vacuum evaporation one deck compound 001 ~ 008 and Bphen are as the electron transfer layer of device, and its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm; (ETL) upper vacuum evaporation A1 layer is as the negative electrode of device on the electron transport layer, and thickness is 150nm.
Above in comparing embodiment, the electron transport material of what the compound as luminescent layer electric transmission adopted the is compound 001-008 represented in synthesis example, except other adopt is method ITO/NPB (40nm)/Ir (ppy) same in comparing embodiment 1 3(10wt%) a kind of in (30nm)/ETL(the compounds of this invention 001-008) (20nm)/LiF (0.5nm)/Al (150nm).The organic luminescent device of structure.
Measure embodiment 1: the luminescent properties of comparative sample Bphen and sample 001-008
Measurement control compounds 1 and sample 001-008 adopt Keithley SMU235, evaluate luminosity, luminous efficiency, glow color.Compd B phen and sample 001-008 is tested equally.The results are shown in Table 3:
Device performance sees the following form:
Can be seen by upper table, adopt the device of the compounds of this invention relative to adopting the device of the Bphen generally used in the industry and obtain good effect, on the basis that driving voltage is relatively low, obtain higher luminous efficiency.
Visible, adopt the compound obtained by embodiment the luminous efficiency of device can be made to improve a lot as electron transport material.Compound prepared by embodiment is owing to introducing the group containing benzothiazole in dibromo phenanthroline position, effectively reduce the LUMO value of material, thus further increase electric transmission and the electron injection ability of material, this is conducive to the improvement of luminescent device performance.
Above to invention has been detailed description; its object is to allow the personage being familiar with this art can understand content of the present invention and be implemented; can not limit the scope of the invention with this; the equivalence change that all spirit according to the present invention are done or modification, all should be encompassed in protection scope of the present invention.

Claims (5)

1. an electroluminescent organic material, is characterized in that, the concrete structure general formula of this material as the formula (1):
................（1）
In general formula (1): R 1, R 2and R 3independently selected from the aromatic group of general formula (2) or (3) 5 ~ 60 carbon atoms containing benzothiazole group;
.................. （2）
................（3）
Wherein, preferred R 4and R 5be selected from hydrogen atom, or be selected from the alkyl of carbon atom number from 1 ~ 6 and alkoxyl group or nothing.
2. electroluminescent organic material according to claim 1, is characterized in that, works as R 1during for formula (2), R 4for nothing, R 5for hydrogen atom; Work as R 1during for formula (3), R 4for nothing; Work as R 1during for formula (2), R 4for nothing, R 5for phenyl; Work as R 1during for formula (2), R 4for phenyl, R 5for nothing; Work as R 2during for formula (2), R 4for nothing, R 5for hydrogen atom; Work as R 2during for formula (3), R 4for nothing; Work as R 2during for formula (2), R 4for nothing, R 5for phenyl; Work as R 2during for formula (2), R 4for phenyl, R 5for nothing; Work as R 3during for formula (2), R 4for nothing, R 5for hydrogen atom; Work as R 3during for formula (3), R 4for nothing; Work as R 3during for formula (2), R 4for nothing, R 5for phenyl; Work as R 3during for formula (2), R 4for phenyl, R 5for nothing.
3. the preparation method of electroluminescent organic material according to claim 1 and 2, is characterized in that, concrete steps and the condition of this preparation method are as follows:
In molar ratio for 2:1 takes bromo benzothiazole amine phenanthroline and the boric acid containing R substituent, mol ratio is that 1:1.25:0.04 takes phenylo boric acid, salt of wormwood and tetrakis triphenylphosphine palladium, and solvent is toluene and water, described ratio is toluene: water is 2:1, be warmed up to 100 DEG C, react 20 hours, cooling, suction filtration, ethanol is washed, separatory, column chromatography, recrystallization, obtains benzothiazolyl phenanthroline compounds.
4. an organic luminescent device, the one or more organic compound layers comprising the first electrode, the second electrode and be placed between described two electrodes, wherein at least one organic compound layer comprise at least one as any one of claim 1-3 the compound that defines.
5. the application of benzothiazolyl phenanthroline compounds in organic electroluminescence device according to any one of claim 1-3, it is characterized in that, described benzothiazolyl phenanthroline compounds is used as electron transport material in described organic electroluminescence device.
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WO2016191914A1 (en) * 2015-05-29 2016-12-08 Dow Global Technologies Llc Organic composition and electronic device comprising organic layer comprising said composition
CN106701063A (en) * 2016-12-19 2017-05-24 三峡大学 Controllable organic solid-state luminescent material as well as preparation method and application of controllable organic solid-state luminescent material
CN114573577A (en) * 2020-12-01 2022-06-03 乐金显示有限公司 Organic compound, and organic light emitting diode and organic light emitting device comprising the same

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