CN107805242A - A kind of pyrazine connection pyrimidine derivatives and its organic luminescent device - Google Patents

A kind of pyrazine connection pyrimidine derivatives and its organic luminescent device Download PDF

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CN107805242A
CN107805242A CN201711048669.8A CN201711048669A CN107805242A CN 107805242 A CN107805242 A CN 107805242A CN 201711048669 A CN201711048669 A CN 201711048669A CN 107805242 A CN107805242 A CN 107805242A
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unsubstituted
substituted
pyrazine
pyrimidine derivatives
aryl
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董秀芹
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of pyrazine connection pyrimidine derivatives and its organic luminescent device, is related to organic optoelectronic materials technology.The present invention connects different groups by joining in pyrazine in connection pyrimidine main body, and so as to obtain a kind of bipolar transmission material, it has, and stronger cavity transmission ability and electron transport ability, heat endurance be good, good film-forming property, and synthesis is simple to operation.It can be applied to be used as hole transmission layer or electron transfer layer in organic luminescent device, can effectively solve the problems, such as that carrier transport is uneven in organic luminescent device, luminous efficiency is low, short life, its organic luminescent device has the advantages of luminous efficiency is high, long lifespan.

Description

A kind of pyrazine connection pyrimidine derivatives and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to a kind of pyrazine connection pyrimidine derivatives and its organic hair Optical device.
Background technology
Organic luminescent device (OLED) shows as a kind of emerging flat panel, and it has, and self-luminous, visual angle be wide, Quan Gu Change, true color, reaction speed are fast, high brightness, low driving voltage, thickness of thin, light weight, can make large scale and curved panel etc. Feature, in recent years, OLED have obtained increasing application in monitor market, turn into Display panel skill most potential at present Art.
Its structure of organic luminescent device be generally comprise negative electrode, anode and between the two and outside organic layer.For Brightness, efficiency and the life-span of organic luminescent device are improved, generally uses sandwich construction in the devices.These sandwich constructions include Luminescent layer and various auxiliary organic layers, the organic photoelectric functional material applied to each organic layer can be roughly divided into two classes from purposes Material：Electric charge injects and transmission material, luminescent material.Further, electric charge injection transmission material is divided into electron injection material, electronics Transmission material, hole-injecting material, hole mobile material, it is mainly equilbrium carrier injection that it, which is acted on, so that electronics and hole Exciton is effectively combined to form in luminescent layer, so it is luminous, improve luminous efficiency.Luminescent material generally comprises material of main part and object On the one hand the effect of dopant material, wherein material of main part is the transmission of equilbrium carrier, another beneficial to the compound of electronics and hole Aspect is then the self-quenching for reducing excessive concentration.Due to the limitation of technology at this stage, electric transmission express delivery is less than hole transport speed Degree, cause luminescent layer electronics and hole-recombination uneven, light-emitting zone is partial to negative electrode, and luminous efficiency is low, device so as to occur The problem of loss is fast, short life.
All in all, following OLED direction be develop high efficiency, high brightness, the long-life, low cost white light parts and Full color display device, but the technological industrialization process still faces many key issues, and how equilbrium carrier injects, and improves Luminous efficiency, extending device service life turns into urgent problem to be solved.
The content of the invention
It is an object of the invention to provide a kind of pyrazine connection pyrimidine derivatives and its organic luminescent device, pyrrole provided by the invention Piperazine connection pyrimidine derivatives are a kind of bipolar materials, have good hole transport and electronic transmission performance, and heat endurance is good, into Film is good, and synthetic method is simple to operation, and the organic luminescent device prepared using pyrazine connection pyrimidine derivatives has good Luminous efficiency and life-span performance.
The invention provides a kind of pyrazine to join pyrimidine derivatives, and its general formula of molecular structure is as shown in chemical formula I：
Wherein, Ar1、Ar2、Ar3、Ar4Do not take independently selected from hydrogen, substituted or unsubstituted C1~C30 alkyl, substitution or C6~C30 aryl in generation, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substitution or One kind in unsubstituted C3~C30 heterocyclic radicals；X1、X2、X3、X4Independently selected from carbon or nitrogen.
Preferably, Ar1、Ar2、Ar3、Ar4Independently selected from hydrogen, substituted or unsubstituted C1~C10 alkyl, substitution or not Substituted C6~C24 aryl, substituted or unsubstituted C6~C36 aryl amines, substitution or the thick aryl of unsubstituted C10~C24, substitution Or one kind in unsubstituted C3~C24 heterocyclic radicals.
Preferably, X1、X2、X3、X4Middle any two is nitrogen.
Preferably, pyrazine of the invention connection pyrimidine derivatives are selected from structure shown in following II-III：
Wherein, Ar1、Ar3Independently selected from hydrogen, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~ It is C30 aryl, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substituted or unsubstituted One kind in C3~C30 heterocyclic radicals；R1、R2Independently selected from substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substitution do not take One kind in C3~C30 heterocyclic radicals in generation.
Preferably, any one of pyrazine of the invention connection pyrimidine derivatives in chemical constitution as follows：
Present invention also offers a kind of organic luminescent device, the organic luminescent device includes negative electrode, anode and is placed in institute State between two electrodes and outside one or more organic matter layers, described organic matter layer contains any pyrrole of the present invention Piperazine joins pyrimidine derivatives.
Preferably, organic matter layer of the present invention includes hole transmission layer, contains in hole transmission layer of the present invention Any pyrazine joins pyrimidine derivatives.
Preferably, organic matter layer of the present invention includes electron transfer layer, contains in electron transfer layer of the present invention Any pyrazine joins pyrimidine derivatives.
Beneficial effects of the present invention：
The present invention provides a kind of pyrazine connection pyrimidine derivatives and its organic luminescent device.The present invention in pyrazine by joining pyrimidine Aryl amine derivatives are connected in structure, wherein the electron withdraw group such as pyrimidine, pyrazine, aryl amine derivatives are electron donating group, the two knot Close and cause pyrazine connection pyrimidine derivatives of the present invention that there is good bipolar transmission performance.
Under the combination, benzene, biphenyl, naphthalene, anthracene, phenanthrene, triphenylene, fluorenes, the fluorenes of spiral shell two, carbazole and its derivative etc. are introduced Substituted radical, it can both increase the molecular weight of compound, be not easy to crystallize so as to improve glass transition temperature, reduce molecule again Coplanarity, it is easy to film forming.
The preparation method of pyrazine connection pyrimidine derivatives of the present invention is simple, and raw material is easy to get, and disclosure satisfy that industrialization demand.
Pyrazine connection pyrimidine derivatives of the present invention can be widely applied in organic luminescent device, can be respectively as hole Transport layer, electron transfer layer, the organic luminescent device prepared using pyrazine of the present invention connection pyrimidine derivatives have good Luminous efficiency and life-span performance.
Embodiment：
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation Example only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, art technology The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to protection scope of the present invention.
The invention provides a kind of pyrazine to join pyrimidine derivatives, and its general formula of molecular structure is as shown in chemical formula I：
Wherein, Ar1、Ar2、Ar3、Ar4Do not take independently selected from hydrogen, substituted or unsubstituted C1~C30 alkyl, substitution or C6~C30 aryl in generation, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substitution or One kind in unsubstituted C3~C30 heterocyclic radicals；X1、X2、X3、X4Independently selected from carbon or nitrogen.
Preferably, Ar1、Ar2、Ar3、Ar4Independently selected from hydrogen, substituted or unsubstituted C1~C10 alkyl, substitution or not Substituted C6~C24 aryl, substituted or unsubstituted C6~C36 aryl amines, substitution or the thick aryl of unsubstituted C10~C24, substitution Or one kind in unsubstituted C3~C24 heterocyclic radicals.
According to the present invention, the substituted alkyl, substitution aryl, substitution aryl amine, substitution thick aryl, substitution Heterocyclic radical, the substituent are independently selected from deuterium, C1-C10Alkyl, C6-C24Aryl or C3-C20Heterocyclic radical.
Preferably, X1、X2、X3、X4Middle any two is nitrogen.
Further preferably, pyrazine connection pyrimidine derivatives of the present invention are selected from the structure shown in following II, III：
Wherein, Ar1、Ar3、Ar4Independently selected from hydrogen, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substitution do not take One kind in C3~C30 heterocyclic radicals in generation；R1、R2Do not take independently selected from substituted or unsubstituted C1~C30 alkyl, substitution or C6~C30 aryl in generation, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substitution or One kind in unsubstituted C3~C30 heterocyclic radicals.
Most preferably, as an example, it is not particularly limited, a kind of pyrazine connection pyrimidine derivatives of the present invention are selected from as follows Any one in shown chemical constitution：
The pyrazine connection pyrimidine derivatives of the present invention synthesize the present invention by a series of Buchward, Suzuki coupling reactions etc. The pyrazine connection pyrimidine derivatives of described chemical structure shown in formula I.
The present invention special limitation no to above-mentioned reaction, it is using popular response well-known to those skilled in the art Can, the preparation method is simple, easily operated.
Present invention also offers a kind of organic luminescent device, the organic luminescent device includes negative electrode, anode and is placed in institute One or more organic matter layers between two electrodes are stated, described organic matter layer contains pyrazine connection pyrimidine derivates of the present invention Thing.
Preferably, the organic matter layer includes hole transmission layer, contains in hole transmission layer of the present invention any Pyrazine joins pyrimidine derivatives.
Preferably, the organic matter layer includes electron transfer layer, contains in electron transfer layer of the present invention any Pyrazine joins pyrimidine derivatives.
OLED structure of the present invention is：ITO is as transparent anode；2-TNATA injects as hole Layer；NPB or of the present invention pyrazines join pyrimidine derivatives as hole transmission layer；3Ph-anthracene/Ir(tpy)3With Make luminescent layer；TPBi or of the present invention pyrazines connection pyrimidine derivatives are used as electron transfer layer；LiF is used as electron injecting layer； Al is used as negative electrode.
Pyrazine connection pyrimidine derivatives of the present invention are used as hole transmission layer respectively, to have manufactured construction same as below Organic luminescent device：
ITO/2-TNATA (50nm)/pyrazine of the present invention connection pyrimidine derivatives (30nm)/3Ph-anthracene： Ir(tpy)3(30nm)/TPBi(30nm)/LiF/(0.5nm)/Al(500nm)。
Pyrazine connection pyrimidine derivatives of the present invention are used as electron transfer layer, to manufacture having for construction same as below Machine luminescent device：
ITO/2-TNATA(50nm)/NPB(30nm)/3Ph-anthracene：Ir(tpy)3(30nm)/it is of the present invention Pyrazine connection pyrimidine derivatives (30nm)/LiF (0.5nm)/Al (500nm).
Pyrazine connection pyrimidine derivatives of the present invention are used as hole transmission layer and electron transfer layer respectively, to have manufactured The organic luminescent device of construction same as below：
ITO/2-TNATA (50nm)/pyrazine of the present invention connection pyrimidine derivatives (30nm)/3Ph-anthracene： Ir(tpy)3(30nm)/pyrazine of the present invention connection pyrimidine derivatives (30nm)/LiF/ (0.5nm)/Al (500nm).
Organic luminescent device of the present invention can be widely applied to Display panel, lighting source, flexible OLED, Electronic Paper, The field such as Organophotoreceptor or OTFT, direction board, signal lamp.
The synthesis of [embodiment 1] compound 1
Step1：5- (5- bromo-pyrazine -2- bases) pyrimidine -2- amine (2.18g, 8.4mmol), bromobenzene are added in reaction vessel (2.86g, 18.2mmol), potassium tert-butoxide (2.83g, 25.2mmol), Pd2(dba)3(0.07g, 0.08mmol), ultrasonic deoxygenation Dimethylbenzene 40mL, stirring and dissolving, displaced air three times, add P (t-Bu)3(0.07g, 0.34mmol), again displaced air three It is secondary, back flow reaction 6h, room temperature is cooled to, adds enough dichloromethane so that product is completely dissolved, excessively a small amount of silica gel funnel, remove Fall catalyst and salt, filtrate is concentrated into thick, crosses column chromatography, obtains intermediate 1-1 (2.24g, 66%).
Step2：Intermediate 1-1 (3.40g, 8.4mmol), diphenylamines (1.56g, 9.2mmol), uncle are added in reaction vessel Butanol potassium (2.83g, 25.2mmol), Pd2(dba)3The dimethylbenzene 40mL of (0.07g, 0.08mmol), ultrasonic deoxygenation, stirring are molten Solution, displaced air three times, add P (t-Bu)3(0.07g, 0.34mmol), again displaced air three times, back flow reaction 6h, cooling To room temperature, enough dichloromethane are added so that product is completely dissolved, excessively a small amount of silica gel funnel, remove catalyst and salt, filtrate Be concentrated into it is thick, cross column chromatography, obtain compound 1 (2.81g, 68%).
The synthesis of [embodiment 2] compound 2
Synthetic method according to compound 1 obtains compound 2 (4.28g, 64%).
The synthesis of [embodiment 3] compound 19
Step1：Aniline (0.75g, 8mmol), the bromo- benzophenanthrenes of 2- (2.05g, 6.67mmol), Pd are added in reactor2 (dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14g, 0.67mmol), NaOt-Bu (2.24g, 20mmol), toluene solution 100mL, reacts 24h under the conditions of 100 DEG C, reaction terminate after with ether and water extraction organic phase, organic layer MgSO4Dry, it is dense Contracting organic matter, cross column chromatography, be recrystallized to give intermediate 19-1 (1.58g, 74%).
Step2：5- (5- bromo-pyrazine -2- bases) pyrimidine -2- amine (2.18g, 8.4mmol), bromobenzene are added in reaction vessel (1.32g, 8.4mmol), potassium tert-butoxide (2.83g, 25.2mmol), Pd2(dba)3(0.07g, 0.08mmol), ultrasonic deoxygenation Dimethylbenzene 40mL, stirring and dissolving, displaced air three times, add P (t-Bu)3(0.07g, 0.34mmol), again displaced air three It is secondary, back flow reaction 6h, room temperature is cooled to, adds enough dichloromethane so that product is completely dissolved, excessively a small amount of silica gel funnel, remove Fall catalyst and salt, filtrate is concentrated into thick, crosses column chromatography, obtains intermediate 19-2 (1.82g, 66%).
Step3：In reaction vessel add intermediate 19-2 (2.76g, 8.4mmol), the bromo- benzophenanthrenes of 2- (2.58g, 8.4mmol), potassium tert-butoxide (2.83g, 25.2mmol), Pd2(dba)3(0.07g, 0.08mmol), the dimethylbenzene of ultrasonic deoxygenation 40mL, stirring and dissolving, displaced air three times, add P (t-Bu)3(0.07g, 0.34mmol), again displaced air three times, backflow 6h is reacted, is cooled to room temperature, enough dichloromethane is added so that product is completely dissolved, excessively a small amount of silica gel funnel, removes catalysis Agent and salt, filtrate be concentrated into it is thick, cross column chromatography, obtain intermediate 19-3 (2.89g, 62%).
Step4：In reaction vessel add intermediate 19-3 (4.66g, 8.4mmol), intermediate 19-1 (2.94g, 9.2mmol), potassium tert-butoxide (2.83g, 25.2mmol), Pd2(dba)3(0.07g, 0.08mmol), the dimethylbenzene of ultrasonic deoxygenation 40mL, stirring and dissolving, displaced air three times, add P (t-Bu)3(0.07g, 0.34mmol), again displaced air three times, backflow 6h is reacted, is cooled to room temperature, enough dichloromethane is added so that product is completely dissolved, excessively a small amount of silica gel funnel, removes catalysis Agent and salt, filtrate be concentrated into it is thick, cross column chromatography, obtain intermediate 19 (3.86g, 58%).
The synthesis of [embodiment 4] compound 21
Synthetic method according to compound 19 obtains compound 21 (4.22g, 61%).
The synthesis of [embodiment 5] compound 31
Synthetic method according to compound 19 obtains compound 31 (2.55g, 62%).
The synthesis of [embodiment 6] compound 46
Step1：In reaction vessel plus 1-1 (3.40g, 8.4mmol), the fluorenes-3- boric acid of 9,9-spiral shell two (3.31g, 9.2mmol), tetra-triphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL, And distilled water 20mL, stir 3h under the conditions of 120 DEG C.Distilled water stops reaction, ethyl acetate extraction after reaction terminates.It is organic Layer is dried with MgSO4.Vacuum distillation is purified to obtain compound 46 (3.67g, 68%) after removing solvent with silicon gel column.
The synthesis of [embodiment 7] compound 48
Synthetic method according to compound 46 obtains compound 48 (2.69g, 63%).
The synthesis of [embodiment 8] compound 51
Synthetic method according to compound 46 obtains compound 51 (2.65g, 61%).
The synthesis of [embodiment 9] compound 96
Synthetic method according to compound 46 obtains compound 105 (2.17g, 64%).
The azepine benzidine compound FD-MS values of synthesis of the embodiment of the present invention are as shown in table 1：
【Table 1】
Embodiment FD-MS
Embodiment 1 M/z=492.15 (C32H24N6=492.21)
Embodiment 2 M/z=796.40 (C56H40N6=796.33)
Embodiment 3 M/z=792.33 (C56H36N6=792.30)
Embodiment 4 M/z=822.28 (C56H38N8=822.32)
Embodiment 5 M/z=490.23 (C32H22N6=490.19)
Embodiment 6 M/z=641.22 (C45H31N5=641.26)
Embodiment 7 M/z=507.11 (C32H21N5S=507.15)
Embodiment 8 M/z=517.18 (C33H23N7=517.20)
Embodiment 9 M/z=403.11 (C24H17N7=403.15)
[comparative example 1] device prepares embodiment：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleaning terminates Ultrasonic washing is dried later in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, evaporation hole passes Defeated layer NPB/30nm, evaporation main body 3Ph-anthracene：Adulterate Ir (tpy)310% mixing/30nm and then evaporation electronics pass Defeated layer TPBi/30nm, negative electrode LiF/0.5nm, Al/500nm.
[embodiment 10] device prepares embodiment：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleaning terminates Ultrasonic washing is dried later in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, evaporation hole passes Compound 21/30nm, the evaporation main body 3Ph-anthracene of the defeated layer embodiment of the present invention 4：Adulterate Ir (tpy)310% is mixed Conjunction/30nm and then evaporation electron transfer layer TPBi/30nm, negative electrode LiF/0.5nm, Al/500nm.
[embodiment 11] device prepares embodiment：
The compound 21 of the embodiment 4 of hole transmission layer in embodiment 10 is replaced by the compound 31 of embodiment 5.
[embodiment 12] device prepares embodiment：
The compound 21 of the embodiment 4 of hole transmission layer in embodiment 10 is replaced by the compound 46 of embodiment 6.
[embodiment 13] device prepares embodiment：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleaning terminates Ultrasonic washing is dried later in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, evaporation hole passes Defeated layer NPB/30nm, evaporation main body 3Ph-anthracene：Adulterate Ir (tpy)310% mixing/30nm and then evaporation electronics pass Compound 48/30nm, negative electrode LiF/0.5nm, Al/500nm of defeated layer embodiments of the invention 7.
[embodiment 14] device prepares embodiment：
The compound 48 of the embodiment 7 of electron transfer layer in embodiment 13 is replaced by the compound 51 of embodiment 8.
[embodiment 15] device prepares embodiment：
The compound 48 of the embodiment 7 of electron transfer layer in embodiment 13 is replaced by the compound 105 of embodiment 9.
[embodiment 16] device prepares embodiment：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleaning terminates Ultrasonic washing is dried later in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, evaporation hole passes Compound 21/30nm, the evaporation main body 3Ph-anthracene of the defeated layer embodiment of the present invention 4：Adulterate Ir (tpy)310% is mixed Conjunction/30nm and then the compound 48/30nm of the evaporation electron transfer layer embodiment of the present invention 7, negative electrode LiF/0.5nm, Al/ 500nm。
[embodiment 17] device prepares embodiment：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleaning terminates Ultrasonic washing is dried later in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode being already prepared to, evaporation hole passes Compound 31/30nm, the evaporation main body 3Ph-anthracene of the defeated layer embodiment of the present invention 5：Adulterate Ir (tpy)310% is mixed The compound 51/30nm of conjunction/30nm and then evaporation electron transfer layer embodiments of the invention 8, negative electrode LiF/0.5nm, Al/ 500nm。
The characteristics of luminescence test result such as table 2 of luminescent device prepared by 10-17 of the embodiment of the present invention and comparative example 1 It is shown.
[table 2]
Result above shows that pyrazine of the invention connection pyrimidine derivatives are applied in organic luminescent device, especially as Hole transmission layer, electron transfer layer, the luminous efficiency of its organic electro-luminance device and life-span are significantly increased, pyrazine of the invention connection Pyrimidine derivatives are luminous organic materials of good performance.
It should be pointed out that the present invention is particularly described with individual embodiments, but before the principle of the invention is not departed from Put, ordinary skill people can carry out the improvement on various forms or details to the present invention, and these improvement also fall into this hair In bright protection domain.

Claims (8)

1. a kind of pyrazine joins pyrimidine derivatives, it is characterised in that its general formula of molecular structure is as shown in chemical formula I：
Wherein, Ar1、Ar2、Ar3、Ar4Independently selected from hydrogen, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6 ~C30 aryl, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substitution or unsubstituted C3~C30 heterocyclic radicals in one kind；X1、X2、X3、X4Independently selected from carbon or nitrogen.
A kind of 2. pyrazine connection pyrimidine derivatives according to claim 1, it is characterised in that Ar1、Ar2、Ar3、Ar4Independently Selected from hydrogen, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C24 aryl, substituted or unsubstituted C6~ One kind in C36 aryl amines, substitution or the thick aryl of unsubstituted C10~C24, substituted or unsubstituted C3~C24 heterocyclic radicals.
A kind of 3. pyrazine connection pyrimidine derivatives according to claim 1, it is characterised in that X1、X2、X3、X4Middle any two For nitrogen.
4. a kind of pyrazine connection pyrimidine derivatives according to claim 1, it is characterised in that the pyrazine connection pyrimidine is selected from such as Structure shown in lower II-III：
Wherein, Ar1、Ar3Independently selected from hydrogen, substituted or unsubstituted C1~C30 alkyl, substitution or unsubstituted C6~C30 virtues Base, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substituted or unsubstituted C3~ One kind in C30 heterocyclic radicals；R1、R2Independently selected from substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~ It is C30 aryl, substituted or unsubstituted C6~C60 aryl amines, substitution or the thick aryl of unsubstituted C10~C30, substituted or unsubstituted One kind in C3~C30 heterocyclic radicals.
A kind of 5. pyrazine connection pyrimidine derivatives according to claim 1, it is characterised in that the azepine benzidine compound Any one in chemical constitution as follows：
6. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes negative electrode, anode and is placed in two electricity Between pole and outside one or more organic matter layers, described organic matter layer contains the pyrrole described in any one of Claims 1 to 5 Piperazine joins pyrimidine derivatives.
7. according to a kind of organic luminescent device described in claim 6, it is characterised in that the organic matter layer passes including hole Defeated layer, the pyrazine connection pyrimidine derivatives described in any one of Claims 1 to 5 are contained in hole transmission layer.
8. according to a kind of organic luminescent device described in claim 6, it is characterised in that the organic matter layer passes including electronics Defeated layer, the pyrazine connection pyrimidine derivatives described in any one of Claims 1 to 5 are contained in electron transfer layer.
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