CN109956961A - A kind of organic compounds containing nitrogen and its application in organic electroluminescence device - Google Patents

A kind of organic compounds containing nitrogen and its application in organic electroluminescence device Download PDF

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CN109956961A
CN109956961A CN201711341657.4A CN201711341657A CN109956961A CN 109956961 A CN109956961 A CN 109956961A CN 201711341657 A CN201711341657 A CN 201711341657A CN 109956961 A CN109956961 A CN 109956961A
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unsubstituted
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叶中华
李崇
张兆超
张小庆
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Jiangsu Sunera Technology Co Ltd
Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

A kind of application the invention discloses organic compounds containing nitrogen and its in organic electroluminescence device, the compound is using azepine spiro fluorene as parent nucleus, such compound has relatively strong rigidity so that compound have the characteristics that it is intermolecular be not easy to crystallize, be not easy to assemble, film forming it is good；Azepine spiro fluorene parent nucleus has stronger electron-withdrawing ability, and branch has electron donation, so that the compounds of this invention has good bipolar transmission property；In addition, the compounds of this invention has high triplet, it can effectively stop energy loss.Therefore, after the compounds of this invention is applied to organic electroluminescence device, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly.

Description

A kind of organic compounds containing nitrogen and its application in organic electroluminescence device
Technical field
The present invention relates to technical field of semiconductors, send out more particularly, to a kind of organic compounds containing nitrogen and its in organic electroluminescence Application in optical device.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is very extensive.Structure of the OLED luminescent device like sandwich, including electrode material film layer, and it is clipped in different electricity Organic functional material between the film layer of pole, various different function materials are overlapped mutually depending on the application collectively constitutes OLED hair together Optical device.As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer function Positive and negative charge in energy film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity Depending on etc. large scales application field extension, still with actual products application require compare, the luminous efficiency of OLED device, use Service life etc. also needs further to be promoted.Proposing high performance research for OLED luminescent device includes: the driving voltage for reducing device, The luminous efficiency for improving device, improves the service life etc. of device.In order to realize OLED device performance continuous promotion, not only The innovation for needing OLED device structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out The functional material of higher performance OLED.It is big that oled light sulfate ferroelectric functional material applied to OLED device can be divided into two from purposes Class, i.e. charge inject transmission material and luminescent material, further, can also inject charge into transmission material and be divided into electron injection transmission Material, electron-blocking materials, hole injection transmission material and hole barrier materials, can also be divided into main body for luminescent material and shine Material and dopant material.In order to make high performance OLED luminescent device, it is desirable that various organic functional materials have good light Electrical characteristics, for example, as charge transport materials, it is desirable that there is good carrier mobility, high-vitrification conversion temperature etc. is made Require material that there is good bipolarity, HOMO/LUMO energy rank appropriate etc. for the material of main part of luminescent layer.
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, applies in industry OLED device structure then includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography A variety of film layers such as defeated layer, electron injecting layer, that is to say, that the photoelectric functional material applied to OLED device is infused including at least hole Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form with rich and more The characteristics of sample.In addition, used photoelectric functional material has stronger for the collocation of the OLED device of different structure Selectivity, performance of the identical material in different structure device, it is also possible to completely totally different.Therefore, for current OLED The industry application requirement of device and the different function film layer of OLED device, the photoelectric characteristic demand of device, it is necessary to which selection is more suitable It closes, OLED functional material or combination of materials with high performance, is just able to achieve the comprehensive of the high efficiency of device, long-life and low-voltage Close characteristic.For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls behind In the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the present invention provides a kind of organic compounds containing nitrogen and its in Organic Electricity Application in electroluminescence device.The compounds of this invention is using azepine spiro fluorene as core, glass transition temperature with higher and molecule heat Stability, suitable HOMO and lumo energy, higher carrier mobility and triplet are applied to OLED device, can Effectively improve luminous efficiency and the service life of device.
Technical scheme is as follows: a kind of organic compounds containing nitrogen, shown in the structure of the compound such as general formula (1):
In general formula (1), Ar is expressed as singly-bound, substituted or unsubstituted C6-C30Arlydene, substituted or unsubstituted C5-C30 Heteroarylidene；
R is expressed as structure shown in general formula (2) or general formula (3):
Wherein, R1、R2Structure shown in selection hydrogen or general formula (4) independently, general formula (5), and R1、R2It is not simultaneously Hydrogen；R3It is expressed as structure shown in general formula (4), general formula (5):
Wherein, a is selected fromX1、X2、X3Independently be expressed as oxygen atom, sulphur atom, C1-10Straight chain Or in the alkylidene of branched alkyl substitution, the alkylidene of aryl substitution, alkyl-substituted imido grpup or the imido grpup of aryl substitution One kind；
R4、R5、R6Independently be expressed as substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or not Substituted xenyl, substituted or unsubstituted furyl, substituted or unsubstituted carbazyl, takes substituted or unsubstituted anthryl Generation or unsubstituted naphthyridines base, substituted or unsubstituted quinolyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrole Piperidinyl, substituted or unsubstituted base, substituted or unsubstituted 9,9- dimethyl fluorenyl, substituted or unsubstituted phenanthryl, substitution Or one in unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazyl Kind；
General formula (4) passes through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key and General formula (2) or general formula (3) bond cyclization.
On the basis of above scheme, the present invention can also do following improvement.
Preferably, a kind of organic compounds containing nitrogen, Ar are expressed as singly-bound, substituted or unsubstituted phenylene, substitution or not Substituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted sub- furans Base, substituted or unsubstituted sub- naphthyridines base, substituted or unsubstituted sub- quinolyl, replaces substituted or unsubstituted sub- carbazyl Or unsubstituted sub- thienyl, substituted or unsubstituted sub-pyridyl group, the sub- pyrimidine radicals of pyridyl group substituted or unsubstituted, substitution or Unsubstituted Asia 9,9- dimethyl fluorenyl, substituted or unsubstituted sub- dibenzofuran group, takes substituted or unsubstituted phenanthrylene One of generation or unsubstituted sub- dibenzothiophene；
Preferably, a kind of organic compounds containing nitrogen, the R are indicated are as follows:
Any one of.
Preferably, a kind of organic compounds containing nitrogen, concrete structure formula are as follows:
The application also provides a kind of organic electroluminescence device, contains including at least one layer of functional layer described nitrogenous organic Compound.
Preferably, a kind of organic electroluminescence device, including luminescent layer, the luminescent layer include described nitrogenous organise Close object.
The present invention also provides a kind of illumination or display elements, including the organic electroluminescence device.
The present invention is beneficial to be had the technical effect that
The compounds of this invention is connected using azepine spiro fluorene as core by aromatic group, such compound has relatively strong rigidity, So that compound have it is intermolecular be not easy to crystallize, be not easy to assemble, film forming is good, glass transition temperature is higher and thermal stability is good Feature；Azepine spiro fluorene parent nucleus has stronger electron-withdrawing ability, and branch has good electron donation, so that chemical combination of the present invention Object has good bipolar transmission property；In addition, the compounds of this invention has high triplet, it can effectively stop energy Loss.
After compound of the present invention is applied to OLED device as organic electroluminescent functional layer material, the electric current of device Efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly, in OLED There is good application effect in luminescent device, there is good industrialization prospect.
Detailed description of the invention
Fig. 1 is the device architecture schematic diagram of the compounds of this invention application；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminous Layer, 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be negative electrode layer；
Fig. 2 is the effect of visualization figure of compound 1HOMO energy level；
Fig. 3 is the effect of visualization figure of compound 1LUMO energy level；
Fig. 4 is the effect of visualization figure of 13 HOMO energy level of compound；
Fig. 5 is the effect of visualization figure of 13 lumo energy of compound；
Fig. 6 is the effect of visualization figure of compound 26HOMO energy level；
Fig. 7 is the effect of visualization figure of 26 lumo energy of compound；
Fig. 8 is the effect of visualization figure of compound CBP HOMO energy level；
Fig. 9 is the effect of visualization figure of compound CBP lumo energy.
Specific embodiment
Raw material used in the embodiment of the present invention passes through purchase and obtains.
The synthesis of 1 compound 1 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material A -1,0.03mol raw material B-1 be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain compound 1, HPLC purity 99.3%, yield 76.3%；
Elemental analysis structure (molecular formula C41H23N3O): theoretical value C, 85.84；H,4.04；N,7.33；Test value: C, 85.82；H,4.05；N,7.34.MS m/z:573.42 [M+H]+, theoretical value: 573.65.
The synthesis of 2 compound 13 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material B-2,0.03mol paradibromobenzene be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain intermediate C-1；
In the there-necked flask of 250mL, lead under nitrogen protection, sequentially adds 0.02mol intermediate C-1,0.03mol connection boric acid Pinacol ester, 0.05mol potassium carbonate, 0.002mol Pd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, 80 DEG C are heated to, is reacted 24 hours, samples contact plate, display is remaining without intermediate C-1, fully reacting；Cooled to room temperature adds There is solid precipitation after water, filter, filter cake is taken to be dried with vacuum oven, then crosses neutral silica gel column, obtain intermediate D-1；
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -1,0.01mol intermediate D- 1,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without intermediate D-1, fully reacting；Cooled to room temperature has after adding water Solid is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 13, HPLC purity 99.6%, yield 63.8%；
Elemental analysis structure (molecular formula C53H32N4): theoretical value C, 87.82；H,4.45；N,7.73；Test value: C, 87.83；H,4.44；N,7.75.MS m/z:724.56 [M+H]+, theoretical value: 724.87.
The synthesis of 3 compound 26 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material A -1,0.03mol raw material B-3 be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain compound 26, HPLC purity 99.3%, yield 76.3%；
Elemental analysis structure (molecular formula C41H23N3O): theoretical value C, 85.84；H,4.04；N,7.33；Test value: C, 85.82；H,4.05；N,7.34.MS m/z:573.42 [M+H]+, theoretical value: 573.65.
The synthesis of 4 compound 34 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material B-4,0.03mol m-dibromobenzene be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain intermediate C-2；
In the there-necked flask of 250mL, lead under nitrogen protection, sequentially adds 0.02mol intermediate C-2,0.03mol connection boric acid Pinacol ester, 0.05mol potassium carbonate, 0.002mol Pd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, 80 DEG C are heated to, is reacted 24 hours, samples contact plate, display is remaining without intermediate C-2, fully reacting；Cooled to room temperature adds There is solid precipitation after water, filter, filter cake is taken to be dried with vacuum oven, then crosses neutral silica gel column, obtain intermediate D-2；
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -1,0.01mol intermediate D- 2,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without intermediate D-2, fully reacting；Cooled to room temperature has after adding water Solid is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 34, HPLC purity 99.6%, yield 63.8%；
Elemental analysis structure (molecular formula C50H33N3): theoretical value C, 88.86；H,4.92；N,6.22；Test value: C, 88.83；H,4.93；N,6.23.MS m/z:675.51 [M+H]+, theoretical value: 675.83.
The synthesis of 5 compound 68 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material A -1,0.03mol raw material B-5 be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain compound 68, HPLC purity 99.3%, yield 76.3%；
Elemental analysis structure (molecular formula C47H28N4): theoretical value C, 87.01；H,4.35；N,8.64；Test value: C, 87.03；H,43.6；N,8.62.MS m/z:648.47 [M+H]+, theoretical value: 648.77.
The synthesis of 6 compound 82 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material B-6,0.03mol m-dibromobenzene be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain intermediate C-3；
In the there-necked flask of 250mL, lead under nitrogen protection, sequentially adds 0.02mol intermediate C-3,0.03mol connection boric acid Pinacol ester, 0.05mol potassium carbonate, 0.002mol Pd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, 80 DEG C are heated to, is reacted 24 hours, samples contact plate, display is remaining without intermediate C-3, fully reacting；Cooled to room temperature adds There is solid precipitation after water, filter, filter cake is taken to be dried with vacuum oven, then crosses neutral silica gel column, obtain intermediate D-3；
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -1,0.01mol intermediate D- 3,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without intermediate D-3, fully reacting；Cooled to room temperature has after adding water Solid is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 82, HPLC purity 99.6%, yield 63.8%；
Elemental analysis structure (molecular formula C50H33N3): theoretical value C, 88.86；H,4.92；N,6.22；Test value: C, 88.83；H,4.93；N,6.23.MS m/z:675.51 [M+H]+, theoretical value: 675.83.
The synthesis of 7 compound 116 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material A -1,0.03mol raw material B-7 be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain compound 116, HPLC purity 99.3%, yield 76.3%；
Elemental analysis structure (molecular formula C41H23N3O2): theoretical value C, 83.52；H,3.93；N,7.13；Test value: C, 83.51；H,3.92；N,7.14.MS m/z:589.32 [M+H]+, theoretical value: 589.65.
The synthesis of 8 compound 132 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 500mL, lead under nitrogen protection, 0.03mol raw material A -1,0.03mol raw material B-8 be added, 250mL toluene is stirred, and 0.09mol potassium tert-butoxide, 0.0015mol Pd is then added2(dba)3, 110 DEG C are heated to, reflux Reaction 24 hours；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam (- 0.09MPa, 85 DEG C), cross neutral silica gel column, Obtain compound 132, HPLC purity 99.3%, yield 76.3%；
Elemental analysis structure (molecular formula C47H28N4O): theoretical value C, 84.92；H,4.25；N,8.43；Test value: C, 84.91；H,4.26；N,8.42.MS m/z:664.54 [M+H]+, theoretical value: 664.77.
The synthesis of 9 compound 149 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add two boron between 0.02mol raw material B-9,0.02mol Perester radical benzene, 0.025mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, 80 DEG C are heated to, is reacted 24 hours, samples contact plate, display is remaining without raw material B-9, fully reacting；Cooled to room temperature adds water After have solid precipitation, filter, take filter cake to be dried with vacuum oven, then cross neutral silica gel column, obtain intermediate D-4；
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -1,0.01mol intermediate D- 4,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without intermediate D-4, fully reacting；Cooled to room temperature has after adding water Solid is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 149, HPLC purity 99.5%, yield 63.4%；
Elemental analysis structure (molecular formula C53H31N3O): theoretical value C, 87.70；H,4.31；N,5.79；Test value: C, 87.68；H,4.30；N,5.82.MS m/z:725.63 [M+H]+, theoretical value: 725.85.
The synthesis of 10 compound 174 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -2,0.01mol raw material B- 10,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without raw material -10, fully reacting；Cooled to room temperature has admittedly after adding water Body is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 174, HPLC purity 99.2%, yield 74.6%；
Elemental analysis structure (molecular formula C47H27N3O): theoretical value C, 86.88；H,4.19；N,6.47；Test value: C, 86.86；H,4.18；N,6.49.MS m/z:649.51 [M+H]+, theoretical value: 649.75.
The synthesis of 11 compound 194 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -2,0.01mol raw material B- 11,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without raw material B-11, fully reacting；Cooled to room temperature has after adding water Solid is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 194, HPLC purity 99.2%, yield 74.6%；
Elemental analysis structure (molecular formula C50H33N3): theoretical value C, 88.86；H,4.92；N,6.22；Test value: C, 88.84；H,4.93；N,6.23.MS m/z:675.56 [M+H]+, theoretical value: 675.83.
The synthesis of 12 compound 202 of embodiment
The synthesis step of compound is as follows:
0.01mol raw material A -1,0.011mol raw material B-12 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 100ml toluene, is heated to reflux 24 Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity 98.6%, yield 72.7%.
Elemental analysis structure (molecular formula C55H46N4): theoretical value C, 86.58；H,6.08；N,7.34；Test value: C, 86.54；H,6.12；N,7.34.MS m/z:763.0 [M+H]+, theoretical value: 763.10.
The synthesis of 13 compound 210 of embodiment
The synthesis step of compound is as follows:
0.01mol raw material A -3,0.011mol raw material B-12 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 100ml toluene, is heated to reflux 24 Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity 98.2%, yield 70.8%.
Elemental analysis structure (molecular formula C47H30N4): theoretical value C, 86.74；H,4.65；N,8.61；Test value: C, 86.76；H,4.67；N,8.57.MS m/z:650.78 [M+H]+, theoretical value: 650.80.
The synthesis of 14 compound 227 of embodiment
The synthesis step of compound is as follows:
0.01mol raw material A -4,0.011mol raw material B-14 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 100ml toluene, is heated to reflux 24 Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity 98.1%, yield 68.5%.
Elemental analysis structure (molecular formula C56H38N4O): theoretical value C, 85.91；H,4.89；N,7.16；O,2.04；Test Value: C, 85.93；H,4.87；N,7.18；O,2.02.MS m/z:782.95 [M+H]+, theoretical value: 782.91.
The synthesis of 15 compound 265 of embodiment
The synthesis step of compound is as follows:
In the there-necked flask of 250mL, leads under nitrogen protection, sequentially add 0.01mol raw material A -2,0.01mol raw material B- 14,0.015mol potassium carbonate, 0.002molPd (PPh3)4With 100ml toluene/water (volume ratio=5:1), it is stirred, is heated to It 80 DEG C, reacts 24 hours, samples contact plate, display is remaining without raw material B-14, fully reacting；Cooled to room temperature has after adding water Solid is precipitated, and filtering takes filter cake to be dried with vacuum oven, then crosses neutral silica gel column, obtains compound 265, HPLC purity 99.1%, yield 71.3%；
Elemental analysis structure (molecular formula C55H38N4): theoretical value C, 87.50；H,5.07；N,7.42；Test value: C, 87.54；H,5.05；N,7.41.MS m/z:754.94 [M+H]+, theoretical value: 754.90.
The compounds of this invention can be used as emitting layer material use, compound 1, compound to preparation of the embodiment of the present invention 13, compound 26, compound 34, compound 68, compound 82, compound 116, compound 132, compound 149, compound 174, compound 194, compound 202 and current material CBP carry out hot property, fluorescence quantum efficiency, singlet-triplet state respectively The measurement of energy level difference (△ Est), testing result are as shown in table 1.
Table 1
Note: thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opens up Pu Kang using Japan The measurement of SR-3 spectroradiometer；Φ f is that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro of U.S.'s marine optics Fiber spectrometer, the test solid fluorescence amount of C-701 integrating sphere and marine optics LLS-LED the light source composition of Lan Fei company, the U.S. Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method are measured)；Cyclic voltammetric stability It is that the redox characteristic of material is observed by cyclic voltammetry to be identified；Test condition: test sample is dissolved in volume ratio For the methylene chloride and acetonitrile mixed solvent of 2:1, concentration 1mg/mL, electrolyte is the tetrabutyl ammonium tetrafluoroborate or hexafluoro of 0.1M The organic solution of phosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrode, is titanium plate to electrode, working electrode is ITO electrode, is followed Ring number is 20 times.The HOMO test value of material uses AC-2 equipment.
By upper table data it is found that the compounds of this invention thermal stability with higher, lesser singlet-triplet Difference, higher Φ f, so that getting a promotion using the compounds of this invention as the OLED device efficiency of dopant material and service life.
The compounds of this invention is fabricated to organic film as luminescent material, vapor deposition.It is excited, is surveyed with the ultraviolet light of 365nm Organic film fluorescence intensity is determined with test angle distribution situation, its anisotropy factor α is measured by optics fitting software.α is smaller, Show that the luminous subconstiuent of the level of organic film dopant material is more, the utilization rate of dopant material radioluminescence is higher.As TADF Material (thermal excitation delayed fluorescence material), the service life of delayed fluorescence is shorter, and triplet state is easy to return singlet by transition between anti-gap, It is quenched so as to avoid triplet state, is able to ascend efficiency and the service life of device.The results are shown in Table 2.
Table 2
Note: organic film carries out double source by ANS evaporated device and steams altogether, and vapor deposition substrate is high saturating quartz glass, and object is mixed Impurity level concentration is 8%.After vapor deposition, (concentration of water and oxygen be less than 1ppm) is packaged in glove box.Sample is logical Superrefraction rate matching fluid is placed in molten silicon semicolumn prism, changes light emitting angle by turntable, spectrum test uses Sphere Optics SMS-500 type spectrometer.The delayed fluorescence service life is tested by the FLS980 transient lifetime of Edinburg instrument Instrument obtains.
As can be seen from Table 2 relative to Traditional dopant material DCJTB, the sub- anisotropy factor that shines of the compounds of this invention It is small, therefore the light extraction efficiency of organic layer can be improved, promote OLED device efficiency.Meanwhile triplet state can be efficiently used and swashed The energy of son improves device efficiency.
Calculate by HOMO, lumo energy of the quantum-mechanical effects software ORCA to the compounds of this invention and go forward side by side Row visualization, calculation method use B3LYP hydridization functional, base group 6-31g (d).The HOMO energy level effect of visualization of compound 1 is such as Shown in Fig. 2；The lumo energy effect of visualization of compound 1 is as shown in Figure 3；The HOMO energy level effect of visualization of compound 13 is as schemed Shown in 4, the lumo energy effect of visualization of compound 13 is as shown in Figure 5；HOMO energy level effect of visualization such as Fig. 6 of compound 26 Shown, the lumo energy effect of visualization of compound 26 is as shown in Figure 7；HOMO energy level effect of visualization such as Fig. 8 of compound CBP Shown, the lumo energy effect of visualization of compound CBP is as shown in Figure 9.
It can see from the spatial distribution of HOMO, LUMO in the molecule, at the HOMO and lumo energy of the compounds of this invention In the state that is spatially separating, HOMO, LUMO degree of overlapping are small, small so as to cause singlet-triplet difference, are conducive to triplet state and swash Son is converted into singlet exciton by thermal excitation, theoretically device internal quantum efficiency can be made to reach 100%.
12-23 and comparative example 1 compound that the present invention will be described in detail synthesizes are in the devices as hair by the following examples The application effect of photosphere material of main part.For embodiment 12-23 compared with comparative example 1, the manufacture craft of the device is identical, and And identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, except that in device Emitting layer material is changed, using the compounds of this invention.The structure composition of each embodiment obtained device such as 3 institute of table Show.The performance test results of each device are as shown in table 4.
2/ hole injection layer of embodiment 12:ITO anode layer, 3 (HAT-CN, thickness 10nm)/hole transmission layer 4 (NPB, thickness 60nm)/luminescent layer 5 (compound 1 and Ir (ppy)3According to the weight ratio blending of 100:5, thickness 40nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).The molecular structural formula of each compound It is as follows:
Specific preparation process is as follows: transparent substrate layer 1 uses transparent material, such as glass；To ito anode layer 2, (film thickness is It 150nm) is washed, i.e., carries out ultraviolet-ozone washing again after successively carrying out neutralizing treatment, pure water, drying to remove The organic residue on the bright surface ITO.On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, steam The HAT-CN that film thickness is 10nm is plated to use as hole injection layer 3.And then the NPB of 60nm thickness is deposited as hole transmission layer 4.After above-mentioned hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent device is made, structure includes OLED luminescent layer 5 The compound 1 of used preparation of the embodiment of the present invention is used as material of main part, Ir (ppy)3As dopant material, dopant material doping Ratio is 9% weight ratio, and luminescent layer film thickness is 40nm.After above-mentioned luminescent layer 5, continue vacuum evaporation electron transport layer materials For TPBI, the vacuum evaporation film thickness of the material is 40nm, this layer is electron transfer layer 6.On electron transfer layer 6, pass through vacuum Evaporation coating device, lithium fluoride (LiF) layer that production film thickness is 1nm, this layer are electron injecting layer 7.On electron injecting layer 7, pass through Vacuum deposition apparatus, aluminium (Al) layer that production film thickness is 80nm, this layer are the use of cathode reflection electrode layer 8.It is complete as described above After OLED luminescent device, anode and cathode is connected with well known driving circuit, the luminous efficiency of measurement device, is shone The I-E characteristic of spectrum and device.
Table 3
Table 4
Number Current efficiency (cd/A) Color LT95 service life (Hr)@10mA/cm2
Embodiment 12 67.5 Green light 45.8
Embodiment 13 64.2 Green light 44.7
Embodiment 14 66.1 Green light 46.3
Embodiment 15 66.8 Green light 47.5
Embodiment 16 65.9 Green light 45.8
Embodiment 17 67.1 Green light 46.4
Embodiment 18 68.5 Green light 51.3
Embodiment 19 70.3 Green light 56.2
Embodiment 20 63.4 Green light 48.5
Embodiment 21 65.9 Green light 50.1
Embodiment 22 71.8 Green light 47.3
Embodiment 23 70.5 Green light 44.8
Comparative example 1 28 Green light 10.5
Note: device detection performance using comparative example 1 as reference,.Current efficiency test data is device in 10mA/cm2's Data；Driving service life (light emission luminance be original intensity 95%) is device in 10mA/cm2Test data, life test system System is the OLED device life-span tester of owner of the invention and Shanghai University's joint development.
Compound of the present invention can be applied and OLED luminescent device as emitting layer material from the results shown in Table 4 Production, and compared with comparative example 1, either efficiency or service life obtain larger improvement than known OLED material, especially The efficiency of device obtains biggish promotion.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.

Claims (7)

1. a kind of organic compounds containing nitrogen, which is characterized in that shown in the structure of the compound such as general formula (1):
In general formula (1), Ar is expressed as singly-bound, substituted or unsubstituted C6-C30Arlydene, substituted or unsubstituted C5-C30Miscellaneous Asia Aryl；
R is expressed as structure shown in general formula (2) or general formula (3):
Wherein, R1、R2Structure shown in selection hydrogen or general formula (4) independently, general formula (5), and R1、R2It is not simultaneously hydrogen；R3 It is expressed as structure shown in general formula (4), general formula (5):
Wherein, a is selected fromX1、X2、X3Independently be expressed as oxygen atom, sulphur atom, C1-10Straight chain or branch One in imido grpup that alkylidene, alkyl-substituted imido grpup or the aryl of alkylidene, aryl substitution that alkyl group replaces replace Kind；
R4、R5、R6Independently be expressed as substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted Xenyl, substituted or unsubstituted anthryl, substituted or unsubstituted furyl, substituted or unsubstituted carbazyl, substitution or Unsubstituted naphthyridines base, substituted or unsubstituted quinolyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridine Base, substituted or unsubstituted base, substituted or unsubstituted 9,9- dimethyl fluorenyl, substituted or unsubstituted phenanthryl, substitution or One of unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazyl；
General formula (4) passes through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key and general formula (2) or general formula (3) bond is cyclic.
2. a kind of organic compounds containing nitrogen according to claim 1, which is characterized in that Ar is expressed as singly-bound, replaces or do not take The phenylene in generation, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, Substituted or unsubstituted furylidene, substituted or unsubstituted sub- naphthyridines base, replaces or not substituted or unsubstituted sub- carbazyl Substituted sub- quinolyl, substituted or unsubstituted sub- thienyl, substituted or unsubstituted sub-pyridyl group, pyridine substituted or unsubstituted It is the sub- pyrimidine radicals of base, substituted or unsubstituted Asia 9,9- dimethyl fluorenyl, substituted or unsubstituted phenanthrylene, substituted or unsubstituted Sub- dibenzofuran group, one of substituted or unsubstituted sub- dibenzothiophene.
3. a kind of organic compounds containing nitrogen according to claim 1, which is characterized in that the R is indicated are as follows:
Any one of.
4. a kind of organic compounds containing nitrogen according to claim 1, which is characterized in that concrete structure formula are as follows:
5. a kind of organic electroluminescence device, which is characterized in that contain any one of claim 1-6 including at least one layer of functional layer The organic compounds containing nitrogen.
6. organic electroluminescence device according to claim 7, including luminescent layer, which is characterized in that the luminescent layer packet Include organic compounds containing nitrogen described in any one of claims 1-6.
7. a kind of illumination or display element, which is characterized in that including such as described in any item organic electroluminescents of claim 7-8 Device.
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CN110734444A (en) * 2018-07-18 2020-01-31 江苏三月光电科技有限公司 compounds with azaspirofluorene as core and application thereof
CN110734445A (en) * 2018-07-18 2020-01-31 江苏三月光电科技有限公司 compounds with azaspirofluorene as core and application thereof
CN113004287A (en) * 2021-02-09 2021-06-22 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN113527297A (en) * 2021-07-19 2021-10-22 上海天马有机发光显示技术有限公司 Organic compound and application thereof
CN114450268A (en) * 2019-10-17 2022-05-06 默克专利有限公司 Material for organic electroluminescent device

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Publication number Priority date Publication date Assignee Title
CN110734444A (en) * 2018-07-18 2020-01-31 江苏三月光电科技有限公司 compounds with azaspirofluorene as core and application thereof
CN110734445A (en) * 2018-07-18 2020-01-31 江苏三月光电科技有限公司 compounds with azaspirofluorene as core and application thereof
CN110734445B (en) * 2018-07-18 2022-03-15 江苏三月科技股份有限公司 Compound with azaspirofluorene as core and application thereof
CN114450268A (en) * 2019-10-17 2022-05-06 默克专利有限公司 Material for organic electroluminescent device
CN113004287A (en) * 2021-02-09 2021-06-22 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN113004287B (en) * 2021-02-09 2022-07-19 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN113527297A (en) * 2021-07-19 2021-10-22 上海天马有机发光显示技术有限公司 Organic compound and application thereof

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