CN106986877B - It is a kind of using double pyrrolo-indoles as the electroluminescent organic material of core and its application - Google Patents

It is a kind of using double pyrrolo-indoles as the electroluminescent organic material of core and its application Download PDF

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CN106986877B
CN106986877B CN201710270160.1A CN201710270160A CN106986877B CN 106986877 B CN106986877 B CN 106986877B CN 201710270160 A CN201710270160 A CN 201710270160A CN 106986877 B CN106986877 B CN 106986877B
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CN106986877A (en
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盛磊
张鑫鑫
王岩
杨丽
林少波
车晓伟
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Valiant Co Ltd
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Abstract

The present invention relates to a kind of using pyrrolo-indole as the electroluminescent organic material of core and its application, has the molecular structure being shown below:Wherein, R1‑R8It is identical and represent H atom or methyl, Ar1And Ar2It is independent to represent one of aromatic substituents, nitrogen-containing heterocycle substituent group.It is provided by the invention that there is molecular mass appropriate, good thin film stability, suitable molecular entergy level by the electroluminescent organic material of core of double pyrrolo-indoles, it can be used as the luminescent layer of OLED device, be applied in field of organic electroluminescence.

Description

It is a kind of using double pyrrolo-indoles as the electroluminescent organic material of core and its application
Technical field
The present invention relates to a kind of electroluminescent organic material and its applications, more particularly to one kind is using double pyrrolo-indoles as core The electroluminescent organic material of the heart and its application.
Background technique
Organic electroluminescent diode (OLED) results from the eighties in last century, it has self-luminous, wide viewing angle, response speed Degree is fast, colour gamut is broad, many advantages, such as Flexible Displays can be achieved, and by the continuous development of more than two decades, which gradually walks To maturation, currently, organic electroluminescent technology, has been widely used in many quotient such as smart phone, flat panel TV, virtual reality In product.
According to the difference of used organic material, OLED device is divided into small molecule devices and two kinds of macromolecule device, is Realization full-color display, needs to make the display unit of three kinds of different colours of red, green, blue respectively, in small molecule OLED device, Blue luminescent device is not mature enough, and device lifetime and efficiency are relatively low, and people pass through ultra clean technology, encapsulation technology, exploitation tool There is blue light material of high glass-transition temperature etc. to improve the service life of blue-light device, and doping techniques and exploitation have the two poles of the earth knot The new material of structure is then the direction for improving device efficiency.
Summary of the invention
The present invention provides one kind for deficiency existing for blue luminescent device in existing small molecule OLED device with double pyrroles Diindyl is electroluminescent organic material and its application of core.
The technical scheme to solve the above technical problems is that
It is a kind of using double pyrrolo-indoles as the electroluminescent organic material of core, which is characterized in that have as shown in formula I Molecular structure:
Wherein, R1-R8It is identical and represent H atom or methyl, Ar1And Ar2It is independent to represent aromatic substituents, contain One of azepine ring substituents.
Further, the Ar1And Ar2It is independently selected from one of flowering structure:
The beneficial effect of electroluminescent organic material provided by the invention is:
1) provided by the invention that there is molecule matter appropriate by the electroluminescent organic material of core of double pyrrolo-indoles Amount, good thin film stability, suitable molecular entergy level, can be used as the luminescent layer of OLED device, are applied to organic electroluminescence and send out In optical arena.
2) using material of the present invention as luminescent layer, the OLED device that TPBI makes as electron transfer layer, device Maximum brightness 2950-6100cd/m2, maximum current efficiency 1.45-2.12cd/A, device efficiency is good, the chromaticity coordinate of device It is a kind of blue-light device that excitation purity is excellent for (0.15-0.19,0.15-0.20).
A kind of organic electroluminescence device is also claimed in the present invention, includes such as preceding institute in the functional layer of the luminescent device The electroluminescent organic material stated.
It further, include foregoing electroluminescent organic material in the luminescent layer of the luminescent device.
Further, the structure of the organic electroluminescence device includes the tin indium oxide (ITO) being sequentially overlapped from below to up Conducting Glass, hole transmission layer (NPB), luminescent layer, electron transfer layer (TPBI), electron injecting layer (LiF) and cathode layer (Al).All functional layers are all made of vacuum evaporation process and are made, the molecule of used some organic compounds in such device Structural formula is as follows.
In the present invention, the functional layer structure of OLED device, it is not limited to which above-mentioned functional layer structure can such as pass in hole Between defeated layer and anode, increase hole injection layer material HAT-CN etc., the functional layer material of OLED device is also not limited to make With above-mentioned material, these materials can be replaced with other materials, can to device performance to be further improved, such as electron transfer layer To be replaced with TpPYPB etc., the molecular structural formula of these materials is as follows:
The beneficial effect of organic electroluminescence device provided by the invention is: effect is more stable, high-efficient, service life It is longer.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic electroluminescence device of the present invention；
In Fig. 1,1, indium tin oxide-coated glass；2, hole transmission layer；3, luminescent layer；4, electron transfer layer；5, electronics is infused Enter layer；6, cathode layer
Specific embodiment
Principles and features of the present invention are described below in conjunction with example, the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the invention.
One, electroluminescent organic material
Lower listed compound C01~C80, is the representative structure for meeting spirit of that invention and principle, it should be understood that list with The specific structure of lower compound is intended merely to preferably explain the present invention, is not limitation of the present invention.
Two, the preparation method of electroluminescent organic material
The preparation of 1 compound C01 of embodiment
1) it is reacted with raw material 1 and generates intermediate 1, reaction equation is as follows:
Specific reaction process are as follows: in 2L there-necked flask, it is added raw material 1 (127g, 0.5mol), DMF (1050g), at 25 DEG C, N- bromo-succinimide (195g, 1.1mol) is added portionwise, 1.5h is finished, 25 DEG C of insulation reaction 4h, is warming up to 40 DEG C, heat preservation 1h is reacted, 25 DEG C is cooled to, reaction solution is slowly poured into 3L deionized water, stirs 1h, is filtered, the elution of 1.5L deionized water, Collect filter cake, cross silicagel column purification, ethyl acetate: petroleum ether=1:3 elution (V/V) further uses recrystallisation from isopropanol, obtains To 1 fine work 117g of intermediate, yield 56%.High resolution mass spectrum, positive ion mode, molecular formula C18H8Br2N2, theoretical value 411.9034 test value 411.9038.
2) it is reacted with intermediate 1 and generates compound C01, reaction equation is as follows:
Specific reaction process are as follows: in 100mL there-necked flask, it is added intermediate 1 (2.06g, 5mmol), phenyl boric acid (1.5g, 12mmol), four triphenylphosphines are added in potassium carbonate (1.76g, 20mmol), toluene (40g), deionized water (15g), nitrogen protection Palladium (0.1g) is warming up to reflux, reacts 12 hours, stops reacting, and cools down, and liquid separation collects organic phase, sloughs solvent, gained crude product Purified using silica gel column chromatography, eluant, eluent is n-hexane: methylene chloride=3:1 (V/V) obtains object C01 crude product, uses change The further sublimation purification of gas-phase deposition system is learned, 300 DEG C of sublimation temperature, obtains 1.4g object C01, yield 70%.High-resolution Mass spectrum, positive ion mode, molecular formula C30H18N2, theoretical value 406.1470, test value 406.1479.Elemental analysis (C30H18N2), Theoretical value C:88.64, H:4.46, N:6.89, measured value C:88.68, H:4.51, N:6.81.
The preparation of 2 compound C03 of embodiment
Using intermediate 1 and 4- biphenylboronic acid as raw material, according to 1 the method for embodiment and following reaction equations, chemical combination is synthesized Object C03, yield 67%.
High resolution mass spectrum, positive ion mode, molecular formula C42H26N2, theoretical value 558.2096, test value 558.2088.Element Analyze (C42H26N2), theoretical value C:90.29, H:4.69, N:5.01, measured value C:90.31, H:4.66, N:5.03.
The preparation of 3 compound C04 of embodiment
Using intermediate 1 and 1- naphthalene boronic acids as raw material, according to 1 the method for embodiment and following reaction equations, compound is synthesized C04, yield 60%.
High resolution mass spectrum, positive ion mode, molecular formula C38H22N2, theoretical value 506.1783, test value 5061787.Element Analyze (C38H22N2), theoretical value C:90.09, H:4.38, N:5.53, measured value C:90.11, H:4.36, N:5.53.
The preparation of 4 compound C07 of embodiment
Using intermediate 1 and fluoranthene -3- boric acid as raw material, according to 1 the method for embodiment and following reaction equations, chemical combination is synthesized Object C07, yield 66%.
High resolution mass spectrum, positive ion mode, molecular formula C50H26N2, theoretical value 654.2096, test value 654.2091.Element Analyze (C50H26N2), theoretical value C:91.72, H:4.00, N:4.28, measured value C:91.71, H:4.01, N:4.28.
The preparation of 5 compound C09 of embodiment
With intermediate 1 and 9,9- dimethyl fluorene -2- boric acid is raw material, according to method described in embodiment 1 and following reactions Formula synthesizes compound C09, yield 58%.
High resolution mass spectrum, positive ion mode, molecular formula C48H34N2, theoretical value 638.2722, test value 638.2727.Element Analyze (C48H34N2), theoretical value C:90.25, H:5.36, N:4.39, measured value C:90.27, H:5.33, N:4.40.
The preparation of 6 compound C12 of embodiment
Using intermediate 1 and N- phenyl carbazole -3- boric acid as raw material, according to method described in embodiment 1 and following reaction equations, Synthesize compound C12, yield 55%.
High resolution mass spectrum, positive ion mode, molecular formula C54H32N4, theoretical value 736.2627, test value 736.2629.Element Analyze (C54H32N4), theoretical value C:88.02, H:4.38, N:7.60, measured value C:88.01, H:4.36, N:7.63.
The preparation of 7 compound C14 of embodiment
Using intermediate 1 and 4- (3- pyridine) phenyl boric acid as raw material, according to method described in embodiment 1 and following reaction equations, Synthesize compound C14, yield 71%.
High resolution mass spectrum, positive ion mode, molecular formula C40H24N4, theoretical value 560.2001, test value 560.2007.Element Analyze (C40H24N4), theoretical value C:85.69, H:4.31, N:9.99, measured value C:85.66, H:4.37, N:9.97.
The preparation of 8 compound C16 of embodiment
Using intermediate 1 and 4- (dimethylamino) phenyl boric acid as raw material, according to method described in embodiment 1 and following reactions Formula synthesizes compound C16, yield 62%.
High resolution mass spectrum, positive ion mode, molecular formula C34H28N4, theoretical value 492.2314, test value 492.2319.Element Analyze (C34H28N4), theoretical value C:82.90, H:5.73, N:11.37, measured value C:82.93, H:5.71, N:11.36.
The preparation of 9 compound C18 of embodiment
Using intermediate 1 and 4- (diphenyl amino) phenyl boric acid as raw material, according to method described in embodiment 1 and following reactions Formula synthesizes compound C18, yield 66%.
High resolution mass spectrum, positive ion mode, molecular formula C54H36N4, theoretical value 740.2940, test value 740.2946.Element Analyze (C54H36N4), theoretical value C:87.54, H:4.90, N:7.56, measured value C:87.55, H:4.93, N:7.52.
The preparation of 10 compound C20 of embodiment
With intermediate 1 and 4- (9,9- dimethyl acridinium base) phenyl boric acid for raw material, according to method described in embodiment 1 under Reaction equation is stated, compound C20, yield 56% are synthesized.
High resolution mass spectrum, positive ion mode, molecular formula C60H44N4, theoretical value 820.3566, test value 820.3561.Element Analyze (C60H44N4), theoretical value C:87.77, H:5.40, N:6.82, measured value C:87.75, H:5.42, N:6.83.
The preparation of 11 compound C21 of embodiment
Using intermediate 1 and diphenylamines as raw material, reacted according to following reaction equations:
Specific reaction process are as follows: in 100mL there-necked flask, it is added intermediate 1 (2.06g, 5mmol), diphenylamines (2.03g, 12mmol), sodium tert-butoxide (1.44g, 15mmol), dimethylbenzene (55mL), N2Protection, addition palladium acetate (0.022g, 0.1mmol), Phosphine ligands 2- dicyclohexyl phosphine -2 ', 6 '-dimethoxy -1,1 '-biphenyl (0.082g, 0.2mmol) are warming up to Reflux reacts 10 hours, stops reacting, and is cooled to 25 DEG C, and 30mL deionized water is added, and stirs 5min, liquid separation, 30mL deionized water It washes organic phase 1 time, collects organic phase, slough solvent, gained crude product is purified using silica gel column chromatography, and eluant, eluent is n-hexane: two Chloromethanes=3:1 (V/V) obtains object C21 crude product, uses the further sublimation purification of chemical gas-phase deposition system, distillation temperature 325 DEG C of degree, obtains 1.9g object C21, yield 64%.
High resolution mass spectrum, positive ion mode, molecular formula C42H28N4, theoretical value 588.2314, test value 588.2311.Element Analyze (C42H28N4), theoretical value C:85.69, H:4.79, N:9.52, measured value C:85.66, H:4.73, N:9.61.
The preparation of 12 compound C23 of embodiment
Using intermediate 1 and N- phenyl -4- benzidine as raw material, closed according to the reaction process of embodiment 11 and following reaction equations At compound C23, yield 69%.
High resolution mass spectrum, positive ion mode, molecular formula C54H36N4, theoretical value 740.2940, test value 740.2949.Element Analyze (C54H36N4), theoretical value C:87.54, H:4.90, N:7.56, measured value C:87.57, H:4.87, N:7.56.
The preparation of 13 compound C24 of embodiment
With intermediate 1 and N- phenyl -9,9- dimethyl fluorenamine for raw material, according to the reaction process of embodiment 11 and following anti- Formula is answered to synthesize compound C24, yield 71%.
High resolution mass spectrum, positive ion mode, molecular formula C60H44N4, theoretical value 820.3566, test value 820.3571.Element Analyze (C60H44N4), theoretical value C:87.77, H:5.40, N:6.82, measured value C:87.75, H:5.41, N:6.84.
The preparation of 14 compound C25 of embodiment
Using intermediate 1 and N- phenyl dibenzofurans -4- amine as raw material, according to the reaction process of embodiment 11 and following anti- Formula is answered to synthesize compound C25, yield 59%.
High resolution mass spectrum, positive ion mode, molecular formula C54H32N4O2, theoretical value 768.2525, test value 768.2521.Member Element analysis (C54H32N4O2), theoretical value C:84.36, H:4.20, N:7.29, O:4.16, measured value C:84.33, H:4.22, N: 7.20 O:4.25.
The preparation of 15 compound C26 of embodiment
Using intermediate 1 and carbazole as raw material, compound is synthesized according to the reaction process of embodiment 11 and following reaction equations C26, yield 55%.
High resolution mass spectrum, positive ion mode, molecular formula C42H24N4, theoretical value 584.2001, test value 584.2009.Element Analyze (C42H24N4), theoretical value C:86.28, H:4.14, N:9.58, measured value C:86.22, H:4.17, N:9.61.
The preparation of 16 compound C29 of embodiment
Using intermediate 1 and phenthazine as raw material, compound is synthesized according to the reaction process of embodiment 11 and following reaction equations C29, yield 63%.
High resolution mass spectrum, positive ion mode, molecular formula C42H24N4O2, theoretical value 616.1899, test value 616.1892.Member Element analysis (C42H24N4O2), theoretical value C:81.80, H:3.92, N:9.09, O:5.19, measured value C:81.81, H:3.97, N: 9.12 O:5.10.
The preparation of 17 compound C31 of embodiment
1) it is reacted with raw material 1 and generates intermediate 2, reaction equation is as follows:
Specific reaction process are as follows: in 1L there-necked flask, be added raw material 1 (76.3g, 0.3mol), methylene chloride (550g), 5 At DEG C, N- bromo-succinimide (58.7g, 0.33mol) is added portionwise, 1.5h is finished, 5 DEG C of insulation reaction 4h, by reaction solution It is slowly poured into 500mL deionized water, stirs 0.5h, liquid separation collects organic phase, sloughs solvent, gained object crude product crosses silicon Rubber column gel column purification, methylene chloride: petroleum ether=1:3 elution (V/V) further uses dehydrated alcohol recrystallization, obtains 2 essence of intermediate Product 47g, yield 47%.
High resolution mass spectrum, positive ion mode, molecular formula C18H9BrN2, theoretical value 331.9949, test value 331.9947.
2) it is that raw material reaction generates intermediate 3 with intermediate 2, reaction equation is as follows:
Specific reaction process are as follows: in 1L there-necked flask, be added intermediate 2 (46.6g, 0.14mol), 1- naphthalene boronic acids (25.8g, 0.15mol), potassium carbonate (41.4g, 0.3mol), toluene (400g), deionized water (120g) under nitrogen protection, add Enter tetra-triphenylphosphine palladium (1.5g), be warming up to reflux, insulation reaction 18h is cooled to 25 DEG C, liquid separation, organic phase desolventizing, gained Crude product crosses silicagel column purification, methylene chloride: petroleum ether=1:3 elution (V/V) further uses dehydrated alcohol recrystallization, obtains 3 fine work 41.8g of intermediate, yield 78.5%.
High resolution mass spectrum, positive ion mode, molecular formula C28H16N2, theoretical value 380.1313, test value 380.1307.
3) it is that raw material reaction generates intermediate 4 with intermediate 3, reaction equation is as follows:
Specific reaction process are as follows: in 1L there-necked flask, it is added intermediate 3 (41g, 0.107mol), methylene chloride (580g), At 25 DEG C, N- bromo-succinimide (21.4g, 0.12mol) is added portionwise, 1.5h is finished, and is warming up to reflux, insulation reaction Reaction solution is slowly poured into 500mL deionized water by 4h, stirs 0.5h, and liquid separation collects organic phase, sloughs solvent, gained target Object crude product crosses silicagel column purification, methylene chloride: petroleum ether=1:3 elution (V/V) further uses re crystallization from toluene, obtains 4 fine work 42.8g of mesosome, yield 87.1%.
High resolution mass spectrum, positive ion mode, molecular formula C28H15BrN2, theoretical value 458.0419, test value 458.0422.
4) it is reacted using intermediate 4 and 2- naphthalene boronic acids as raw material and generates compound C31, reaction equation is as follows:
Specific reaction process is as follows: in 100mL there-necked flask, being added intermediate 4 (2.23g, 5mmol), 2- naphthalene boronic acids (1.03g, 6mmol), potassium carbonate (1.76g, 20mmol), toluene (40g), deionized water (15g), nitrogen protection are added four or three Phenylphosphine palladium (0.1g) is warming up to reflux, reacts 12 hours, stops reacting, and cools down, and liquid separation collects organic phase, sloughs solvent, institute Crude product is obtained to purify using silica gel column chromatography, eluant, eluent is n-hexane: methylene chloride=3:1 (V/V) obtains object C31 crude product, Using the further sublimation purification of chemical gas-phase deposition system, 325 DEG C of sublimation temperature, 1.5g object C31, yield 59% are obtained.
High resolution mass spectrum, positive ion mode, molecular formula C38H22N2, theoretical value 506.1783, test value 506.1786.Element Analyze (C38H22N2), theoretical value C:90.09, H:4.38, N:5.53, measured value C:90.11, H:4.33, N:5.56.
The preparation of 18 compound C33 of embodiment
Using intermediate 4 and 4- (1- naphthalene) phenyl boric acid as raw material, according to method described in step 4) in embodiment 17 under State reaction equation synthesis compound C33, yield 71%.
High resolution mass spectrum, positive ion mode, molecular formula C44H26N2, theoretical value 582.2096, test value 582.2091.Element Analyze (C44H26N2), theoretical value C:90.69, H:4.50, N:4.81, measured value C:90.62, H:4.53, N:4.85.
The preparation of 19 compound C34 of embodiment
Using intermediate 4 and 4- phenylnaphthalene -1- boric acid as raw material, according to method described in step 4) in embodiment 17 and following Reaction equation synthesizes compound C34, yield 68%.
High resolution mass spectrum, positive ion mode, molecular formula C44H26N2, theoretical value 582.2096, test value 582.2090.Element Analyze (C44H26N2), theoretical value C:90.69, H:4.50, N:4.81, measured value C:90.62, H:4.54, N:4.84.
The preparation of 20 compound C36 of embodiment
Using intermediate 4 and 9- phenanthrene boric acid as raw material, according to method described in step 4) in embodiment 17 and following reaction equations Synthesize compound C36, yield 57%.
High resolution mass spectrum, positive ion mode, molecular formula C42H24N2, theoretical value 556.1939, test value 556.1937.Element Analyze (C42H24N2), theoretical value C:90.62, H:4.35, N:5.03, measured value C:90.66, H:4.34, N:5.00.
The preparation of 21 compound C39 of embodiment
With intermediate 4 and 9, two fluorenes -2- boric acid of 9'- spiral shell is raw material, according to method described in step 4) in embodiment 17 and Following reaction equations synthesize compound C39, yield 50%.
High resolution mass spectrum, positive ion mode, molecular formula C53H30N2, theoretical value 694.2409, test value 694.2411.Element Analyze (C53H30N2), theoretical value C:91.62, H:4.35, N:4.03, measured value C:91.66, H:4.33, N:4.01.
The preparation of 22 compound C41 of embodiment
Using intermediate 4 and diphenylamines as raw material, compound C41 is synthesized according to following reaction formula:
Specific reaction process is as follows: in 100mL there-necked flask, being added intermediate 4 (2.30g, 5mmol), diphenylamines (1.02g, 6mmol), sodium tert-butoxide (1.44g, 15mmol), dimethylbenzene (50mL), N2Protection, addition palladium acetate (0.022g, 0.1mmol), Phosphine ligands 2- dicyclohexyl phosphine -2 ', 6 '-dimethoxy -1,1 '-biphenyl (0.082g, 0.2mmol) are warming up to Reflux reacts 10 hours, stops reacting, and is cooled to 25 DEG C, and 30mL deionized water is added, and stirs 5min, liquid separation, 30mL deionized water It washes organic phase 1 time, collects organic phase, slough solvent, gained crude product is purified using silica gel column chromatography, and eluant, eluent is n-hexane: two Chloromethanes=3:1 (V/V) obtains object C41 crude product, uses the further sublimation purification of chemical gas-phase deposition system, distillation temperature 315 DEG C of degree, obtains 1.3g object C41, yield 48%.
High resolution mass spectrum, positive ion mode, molecular formula C40H25N3, theoretical value 547.2048, test value 547.2041.Element Analyze (C40H25N3), theoretical value C:87.73, H:4.60, N:7.67, measured value C:87.70, H:4.62, N:7.68.
The preparation of 23 compound C44 of embodiment
Using intermediate 4 and N- phenyl dibenzofurans -4- amine as raw material, according to method described in embodiment 22 and following anti- Formula is answered to synthesize compound C44, yield 59%.
High resolution mass spectrum, positive ion mode, molecular formula C46H27N3O, theoretical value 637.2154, test value 637.2149.Member Element analysis (C46H27N3O), theoretical value C:86.63, H:4.27, N:6.59, O:2.51, measured value C:86.61, H:4.30, N: 6.61 O:2.48.
The preparation of 24 compound C46 of embodiment
1) it is raw material with intermediate 2, is synthesized according to the method for step 2) in following reaction formula and embodiment 17 and step 3) Intermediate 5:
High resolution mass spectrum, positive ion mode, molecular formula C28H15BrN2, theoretical value 458.0419, test value 458.0416.
2) described according to following reaction formula and 17 step 4) of embodiment using intermediate 5 and 6- phenylnaphthalene -2- boric acid as raw material Method synthesize compound C46, yield 56%.
High resolution mass spectrum, positive ion mode, molecular formula C44H26N2, theoretical value 582.2096, test value 582.2089.Element Analyze (C44H26N2), theoretical value C:90.69, H:4.50, N:4.81, measured value C:90.65, H:4.53, N:4.82.
The preparation of 25 compound C48 of embodiment
Using intermediate 5 and 9- phenanthrene boric acid as raw material, closed according to method described in 17 step 4) of following reaction formula and embodiment At compound C48, yield 55%.
High resolution mass spectrum, positive ion mode, molecular formula C42H24N2, theoretical value 556.1939, test value 556.1934.Element Analyze (C42H24N2), theoretical value C:90.62, H:4.35, N:5.03, measured value C:90.65, H:4.32, N:5.03.
The preparation of 26 compound C50 of embodiment
Using intermediate 5 and N- phenyl-2-naphthylamine as raw material, according to side described in 17 step 4) of following reaction formula and embodiment Method synthesizes compound C50, yield 47%.
High resolution mass spectrum, positive ion mode, molecular formula C44H27N3, theoretical value 597.2205, test value 597.2211.Element Analyze (C44H27N3), theoretical value C:88.42, H:4.55, N:7.03, measured value C:88.46, H:4.52, N:7.02.
The preparation of 27 compound C52 of embodiment
1) intermediate 6 is generated according to the step 1) of following reaction formula and embodiment 1 with raw material 2:
2) it using intermediate 6 and 4- tert-butylbenzeneboronic acid as raw material, is synthesized according to the step 4) of following reaction formula and embodiment 1 Compound C52, yield 62%.
The preparation of 28 compound C53 of embodiment
Using intermediate 6 and 4- biphenylboronic acid as raw material, compound is synthesized according to the step 4) of following reaction formula and embodiment 1 C53, yield 66%.
High resolution mass spectrum, positive ion mode, molecular formula C50H42N2, theoretical value 670.3348, test value 670.3341.Element Analyze (C50H42N2), theoretical value C:89.51, H:6.31, N:4.18, measured value C:89.49, H:6.33, N:4.18.
The preparation of 29 compound C58 of embodiment
Using intermediate 6 and 9- phenanthrene boric acid as raw material, compound is synthesized according to the step 4) of following reaction formula and embodiment 1 C58, yield 61%.
High resolution mass spectrum, positive ion mode, molecular formula C54H42N2, theoretical value 718.3348, test value 718.3351.Element Analyze (C54H42N2), theoretical value C:90.21, H:5.89, N:3.90, measured value C:90.24, H:5.86, N:3.90.
The preparation of 30 compound C60 of embodiment
Using intermediate 6 and 1- pyrene boric acid as raw material, compound is synthesized according to the step 4) of following reaction formula and embodiment 1 C60, yield 63%.
High resolution mass spectrum, positive ion mode, molecular formula C58H42N2, theoretical value 766.3348, test value 766.3352.Element Analyze (C58H42N2), theoretical value C:90.83, H:5.52, N:3.65, measured value C:90.84, H:5.57, N:3.59.
The preparation of 31 compound C61 of embodiment
Using intermediate 6 and 4- (9- carbazole) phenyl boric acid as raw material, synthesized according to the step 4) of following reaction formula and embodiment 1 Compound C61, yield 58%.
High resolution mass spectrum, positive ion mode, molecular formula C62H48N4, theoretical value 848.3879, test value 848.3876.Element Analyze (C62H48N4), theoretical value C:87.70, H:5.70, N:6.60, measured value C:87.74, H:5.68, N:6.58.
The preparation of 32 compound C66 of embodiment
1) synthetic intermediate 7: being raw material with raw material 2, according to following reaction formula and referring to the step 1) -3 of embodiment 17) it closes At intermediate 7；
2) using intermediate 7 and 2- naphthalene boronic acids as raw material, the method referring to described in step 4) in embodiment 17 is closed
High resolution mass spectrum, positive ion mode, molecular formula C48H38N2, theoretical value 618.3035, test value 618.3038.Element Analyze (C48H38N2), theoretical value C:89.28, H:6.19, N:4.53, measured value C:89.27, H:6.22, N:4.51.
The preparation of 33 compound C68 of embodiment
Using intermediate 7 and 4- (1- naphthalene) phenyl boric acid as raw material, the synthesis of the method referring to described in step 4) in embodiment 17 Compound C68, yield 56%, reaction process is as follows:
High resolution mass spectrum, positive ion mode, molecular formula C52H42N2, theoretical value 694.3348, test value 694.3341.Element Analyze (C52H42N2), theoretical value C:89.88, H:6.09, N:4.03, measured value C:89.86, H:6.12, N:4.02.
The preparation of 34 compound C70 of embodiment
Using intermediate 7 and fluoranthene -3- boric acid as raw material, the method referring to described in step 4) in embodiment 17 synthesizes compound C70, yield 55%, reaction process is as follows:
High resolution mass spectrum, positive ion mode, molecular formula C52H40N2, theoretical value 692.3191, test value 692.3197.Element Analyze (C52H40N2), theoretical value C:90.14, H:5.82, N:4.04, measured value C:90.17, H:5.81, N:4.02.
The preparation of 35 compound C72 of embodiment
With intermediate 7 and 9,9- dimethyl fluorene -2- boric acid is raw material, and the method referring to described in step 4) in embodiment 17 is closed At compound C72, yield 62%, reaction process is as follows:
7 9,9- dimethyl fluorene -2- boronic acid compounds C72 of intermediate
High resolution mass spectrum, positive ion mode, molecular formula C51H44N2, theoretical value 684.3504, test value 684.3507.Element Analyze (C51H44N2), theoretical value C:89.43, H:6.48, N:4.09, measured value C:89.46, H:6.47, N:4.07.
The preparation of 36 compound C75 of embodiment
Using intermediate 7 and terphenyl -4- boric acid as raw material, the method referring to described in step 4) in embodiment 17 synthesizes chemical combination Object C75, yield 60%, reaction process is as follows:
High resolution mass spectrum, positive ion mode, molecular formula C54H44N2, theoretical value 720.3504, test value 720.3510.Element Analyze (C54H44N2), theoretical value C:89.96, H:6.15, N:3.89, measured value C:89.99, H:6.11, N:3.90.
The preparation of 37 compound C80 of embodiment
1) synthetic intermediate 8 are raw material with raw material 2, according to following reaction formula and referring to the step 1) -3 of embodiment 17) it closes At intermediate 8；
2) with intermediate 8 and 9,9- dimethyl fluorene -2- phenanthrene boric acid is raw material, the side referring to described in step 4) in embodiment 17 Method synthesizes compound C80, and yield 60%, reaction process is as follows:
High resolution mass spectrum, positive ion mode, molecular formula C51H44N2, theoretical value 684.3504, test value 684.3507.Element Analyze (C51H44N2), theoretical value C:89.43, H:6.48, N:4.09, measured value C:89.44, H:6.46, N:4.10.
Three, organic electroluminescence device
We have chosen compound C03, compound C04, compound C12, compound C16, compound C18, compound C21, compound C23, compound C26, compound C33, compound C34, compound C39, compound C41, compound C44, change Close object C50, compound C53, compound C58, compound C65, compound C66, compound C70, compound C75, compound C76, compound C80 make organic electroluminescence device as emitting layer material, and device architecture should be managed as shown in attached drawing one Solution, device implementation process with as a result, being intended merely to preferably explain the present invention, not limitation of the present invention.
Organic electroluminescence device the preparation method is as follows:
A) it cleans ITO (tin indium oxide) glass: cleaning each 30 points of ito glass with deionized water, acetone, EtOH Sonicate respectively Then clock is handled 5 minutes in plasma cleaner；
B) the vacuum evaporation hole transmission layer NPB on anode ito glass, with a thickness of 50nm；
C) on hole transmission layer NPB, vacuum evaporation luminescent layer compound C03, with a thickness of 30nm；
D) on luminescent layer, TPBI of the vacuum evaporation as electron transfer layer, with a thickness of 30nm；
E) on electron transfer layer, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm；
F) on electron injecting layer, vacuum evaporation cathode Al, with a thickness of 100nm.
The structure of the device one of embodiment 1 is ITO/NPB (50nm)/compound C03 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure < 1.0X 10-3Pa, device one open bright voltage, maximum current efficiency, The photooptical datas such as excitation purity are listed in table 1 hereinafter.Embodiment 2-22 respectively with compound C04, compound C12, compound C16, Compound C18, compound C21, compound C23, compound C26, compound C33, compound C34, compound C39, compound C41, compound C44, compound C50, compound C53, compound C58, compound C65, compound C66, compound C70, change It closes object C75, compound C76, compound C80 and replaces compound C03, according to the method described above, make organic electroluminescence device two To device 22, device two to the structure of device 22, respectively ITO/NPB (50nm)/compound C04- compound C80 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device one to device 22 open bright voltage, maximum current effect The photooptical datas such as rate, excitation purity are as shown in table 1 below.
It can be seen that from the data in table 1 using material provided by the invention as luminescent layer, TPBI is as electron transfer layer The OLED device of production, the maximum brightness range of device are 2950-6100cd/m2, maximum current efficiency is 1.45-2.12cd/ A, device efficiency is good, and it is a kind of blue light device that excitation purity is excellent that the chromaticity coordinate of device, which is (0.15-0.19,0.15-0.20), Part.
1 device one of table to device 22 photooptical data table
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.

Claims (5)

1. a kind of using double pyrrolo-indoles as the electroluminescent organic material of core, which is characterized in that have and divide as shown in formula I Minor structure:
Wherein, R1-R8It is identical and represent H atom or methyl, the Ar1And Ar2It is independently selected from one of flowering structure:
2. a kind of using double pyrrolo-indoles as the electroluminescent organic material of core, which is characterized in that have point as follows Minor structure:
3. a kind of organic electroluminescence device, which is characterized in that comprising in claim 1-2 in the functional layer of the luminescent device Described in any item electroluminescent organic materials.
4. organic electroluminescence device according to claim 3, which is characterized in that the functional layer refers to luminescent layer.
5. organic electroluminescence device according to claim 4, which is characterized in that its structure includes successively folding from below to up Indium tin oxide-coated glass substrate, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and the cathode layer added.
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