CN107586294A - High Tg organic electronics transmission apparatus - Google Patents
High Tg organic electronics transmission apparatus Download PDFInfo
- Publication number
- CN107586294A CN107586294A CN201610539848.0A CN201610539848A CN107586294A CN 107586294 A CN107586294 A CN 107586294A CN 201610539848 A CN201610539848 A CN 201610539848A CN 107586294 A CN107586294 A CN 107586294A
- Authority
- CN
- China
- Prior art keywords
- organic
- layer
- transmission apparatus
- compound
- requirement
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000005540 biological transmission Effects 0.000 title claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 29
- 239000004065 semiconductor Substances 0.000 claims abstract description 25
- 239000012044 organic layer Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 238000005401 electroluminescence Methods 0.000 claims abstract description 12
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 55
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 6
- -1 naphthylphenyl Chemical group 0.000 claims description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 abstract description 6
- 230000000877 morphologic effect Effects 0.000 abstract description 4
- 239000011368 organic material Substances 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 2
- 150000002220 fluorenes Chemical class 0.000 abstract 1
- 230000005684 electric field Effects 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HCADTXOJVIBENC-UHFFFAOYSA-N C1=C(c2ccccc2)c(ccc2c3nccc2-c2ccccc2)c3NC1c1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 Chemical compound C1=C(c2ccccc2)c(ccc2c3nccc2-c2ccccc2)c3NC1c1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 HCADTXOJVIBENC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical group [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HPYXZFQWIQFKCB-UHFFFAOYSA-N c(cc1)ccc1-c1ccnc2c1ccc(c(-c1ccccc1)c1)c2nc1-c1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 Chemical compound c(cc1)ccc1-c1ccnc2c1ccc(c(-c1ccccc1)c1)c2nc1-c1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 HPYXZFQWIQFKCB-UHFFFAOYSA-N 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Abstract
The present invention relates to high Tg organic electronics transmission apparatus, and comprising anode, negative electrode and organic layer, the anode and negative electrode are metal, inorganic matter or organic compound；The organic layer has the compound of formula (I) structure, wherein, the fluorenes link position of 9,9' spiral shell two is 1,2,3, or 4；Wherein, Ar1、Ar2Independently it is expressed as the C6 C25 aryl of unsubstituted or C1 C6 substitutions.Material experiment shows that the compound described in formula (I) of the present invention has high glass-transition temperature, hence it is demonstrated that the compound described in formula (I) of the present invention is the organic material of high morphological stability.Device experimental shows, the only electronics organic semiconductor diodes device and organic electroluminescence device prepared using the Organic Electron Transport Material of the present invention is functional and stably, device lifetime length.
Description
Technical field
The present invention relates to a kind of high Tg organic electronics transmission apparatus, using new Organic Electron Transport Material, by true
Sky is deposited into film preparation and obtained, including only electronics organic semiconductor diodes device and organic electroluminescence device.
Background technology
Only electronics organic semiconductor diodes device is one kind of single charge carrier device, is used for as power semiconductor arrangement
The switch or rectifier of intelligent digital power integrated circuit.Wherein electron transport material of the invention can also be applied to organic electroluminescence
Luminescent device and field-effect transistor.
Only electronics organic semiconductor diodes device is to lead between the electrode of two metals, inorganic matter or organic compound
The device for crossing spin coating or depositing one or more layers organic material and preparing.One classical one layer only pole of electronics organic semiconductor two
Tube device includes anode, electron transfer layer and negative electrode.Passed in multilayer only electronics organic semiconductor diodes device anode and electronics
Hole blocking layer can be added between defeated layer, and electron injecting layer can be added between electron transfer layer and negative electrode.Hole barrier
Layer, electron transfer layer and electron injecting layer are respectively by hole barrier materials, electron transport material and electron injection material composition.Even
After being connected to the voltage arrival cut-in voltage of only electronics organic semiconductor diodes device, electronics is through electric transmission as caused by negative electrode
Layer is transferred to anode, on the contrary, hole can not be injected from anode.Electric transmission only in electronics organic semiconductor diodes device
Material may be used on other semiconductor devices such as organic electroluminescence device.Organic electroluminescence device market is huge, thus surely
Application and popularization of fixed, the efficient Organic Electron Transport Material to organic electroluminescence device play an important roll, and are also simultaneously
The active demand of the application of organic electroluminescent large area Display panel.
The existing more electron transport material used of in the market is to bathophenanthroline (bathophenanthroline, BPhen)
With bathocuproine (bathocuproine, BCP), can substantially meet the market demand of organic electroluminescence panel, but its efficiency and
Stability still needs further to be improved.Analysis (sees below formula, the minute surface of molecular structure is empty from BPhen and BCP molecular structure
Line represents), its symmetrical structure can be such that molecule tendency stacks regularly, and the time may be readily formed as crystallizing later.Electron transport material
Once crystallization, intermolecular charge transtion mechanism follow the noncrystalline membrane mechanism in normal operation to differ, are led to electric transmission
Performance change.If the material of BPhen asymmetric molecular structures uses in organic electroluminescence device, the time can make whole later
Device conducts performance change, make electronics and hole charge mobility unbalance, be led to that device efficiency declines, it is also possible in device
Middle generation partial short-circuit, influences device stability, or even make component failure.(bibliography Journal of Applied
Physics 80,2883(1996)；doi:10.1063/1.363140)
The content of the invention
The defects of for above-mentioned material, the present invention provide a kind of Organic Electron Transport Material system using high morphological stability
Only electronics organic semiconductor diodes device of standby long-life.
High Tg organic electronics transmission apparatus, comprising anode, negative electrode and organic layer, the anode and negative electrode are metal, inorganic
Thing or organic compound；The organic layer has the compound of formula (I) structure,
Wherein, the fluorenes link position of 9,9'- spiral shells two is 1-, 2-, 3-, or 4- position；Wherein, Ar1、Ar2Independently it is expressed as not taking
Generation or the C6-C25 aryl of C1-C6 substitutions.
It is preferred that：Ar1, Ar2Independently it is expressed as the substitution of C1-C5 alkyl either phenyl substitution or unsubstituted phenyl, naphthalene
Base, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group substitute or unsubstituting aromatic yl) fluorenyl or 9,9- are Spirofluorene-based.
It is preferred that：Wherein, the fluorenes link position of 9,9'- spiral shells two is 2- or 4- positions；Wherein, Ar1、Ar2Phenyl is independently expressed as,
Tolyl, xylyl, naphthyl, methyl naphthalene, xenyl, diphenyl phenyl, naphthylphenyl, diphenyl xenyl, (9,9- dioxanes
Base) fluorenyl, (9,9- dimethyl substitute or unsubstituted phenyl) fluorenyl, 9,9- is Spirofluorene-based.
It is preferred that：Ar1、Ar2It is expressed as phenyl.
It is preferred that：The fluorenes link position of 9,9'- spiral shells two is 2- or 4- positions；Compound described in formula (I) is having structure compound：
The high Tg organic electronics transmission apparatus is that only electronics organic semiconductor diodes device, the organic layer at least wraps
Include one layer of electron transfer layer.
The high Tg organic electronics transmission apparatus is organic electroluminescence device, and the organic layer comprises at least one layer and lighted
Layer.
The luminescent layer is the host-guest system system or single luminescent material body being made up of material of main part and guest materials
System.
The organic layer also includes one layer or two layers in hole transmission layer, electron injecting layer.
It is hole injection layer that the organic layer, which also includes, hole transmission layer, one layer in hole blocking layer, electron injecting layer
Or multilayer.
Contain the compound described in formula (I) in the hole transmission layer, electron transfer layer and/or luminescent layer.
The gross thickness of the organic layer is 1-1000nm, preferably 1-500nm, more preferably 5-300nm.
The organic layer can be crossed by steaming or spin coating forms film.
As mentioned above, the compound described in formula of the invention (I) is as follows, but is not limited to cited structure：
Material experiment shows that the compound described in formula (I) of the present invention has high glass-transition temperature, hence it is demonstrated that this hair
Compound described in bright formula (I) has the organic material of high morphological stability.Device experimental shows, uses the organic electronic of the present invention
Only electronics organic semiconductor diodes device and organic electroluminescence device prepared by transmission material is functional and stably, device
Long lifespan.
Brief description of the drawings
Fig. 1 is the device junction composition of the present invention,
Wherein 10 are represented as glass substrate, and 20 are represented as anode, and 30 are represented as hole blocking layer, and 40 are represented as electric transmission
Layer, 50 are represented as electron injecting layer, and 60 are represented as negative electrode.
Fig. 2 is compound 21H NMR scheme.
Fig. 3 is compound 213C NMR scheme.
Fig. 4 is that the HPLC of compound 2 schemes.
Fig. 5 is that the TGA of compound 2 schemes.
Fig. 6 is that the DSC of compound 2 schemes.
Fig. 7 is embodiment 2, embodiment 3, current density and the electric-field intensity graph of a relation of embodiment 4
Fig. 8 is comparative example 1, current density and the electric-field intensity graph of a relation of comparative example 2
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 2
Reaction is launched：Tri- mouthfuls of reaction bulbs of 3L, magnetic agitation and low-reading thermometer are assembled, nitrogen purge 3 times, it is bromo- to add 2-
The fluorenes of 9,9'- spiral shell two (20.0g, 50.6mmol), anhydrous tetrahydro furan (1000mL), to dissolving, liquid nitrogen/ethanol bath cools down for stirring
To -90~-80 DEG C, the hexane solution (42mL, 1.25M) of n-BuLi is slowly added dropwise, below -75 DEG C of controlling reaction temperature,
After n-BuLi is all added dropwise, continue react 0.5h, be then added dropwise 4,7- diphenyl phenanthroline (25.0g, 75mmol)/
THF solution (1000mL), control below -75 DEG C of temperature, after being added dropwise, 8h is stirred at room temperature after adding solution, adds water (10mL)
Then 24h is stirred in atmosphere.After stopping reaction, THF is spin-dried for, adds water and ethyl acetate extraction, organic layer merges, and use is anhydrous
Magnesium sulfate dry after filter, filtrate is beaten after being spin-dried for acetone, filter, filtering medium be containing compound 2 (12.46g, yield 38.1%,
HPLC purity 99.2%).7.40g crude products are in vacuum (4x 10-5Torr) it is yellowish to obtain 5.11g after the completion of distilling for 320 DEG C of heating
Color powdery product, purity 99.5%.
Embodiment 2
The only preparation of electronics organic semiconductor diodes device 1
Only electronics organic semiconductor diodes device is prepared using the Organic Electron Transport Material of the present invention
First, electrically conducting transparent ito glass substrate 10 (carrying anode 20 above) is passed through successively：Detergent solution and deionization
Water, ethanol, acetone, deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, steamed on ITO and cross the thick BCP of 5nm as hole blocking layer 30.
Then, steaming crosses the thick compounds 2 of 100nm and is used as electron transfer layer 40 on hole blocking layer.
Then, steam on the electron transport layer and cross the thick lithium fluoride of 1nm as electron injecting layer 50.
Finally, steamed on electron injecting layer and cross the thick aluminium of 100nm as device cathodes 60.
Electric current (space charge limited current, SCLC) current density and electric field are limited by using space
The relation of intensity such as formula (1)：
Wherein, J is current density (mA cm-2), ε is relative dielectric constant (the usual value of organic material be 3), ε0It is true
Empty dielectric constant (8.85 × 10-14 C V-1 cm-1), E is electric-field intensity (V cm-1), L is the thickness (cm) of sample in device,
μ0It is the charge mobility (cm under zero electric field2 V-1 s-1), β is the Poole-Frenkel factors, represents mobility with electric-field intensity
The speed degree of change.
Prepared device is in E=1x 106Vcm-1Applied electric field under electron mobility be 4.25x 10-4cm2V-1s-1。
Structural formula described in device
Embodiment 2
The only preparation of electronics organic semiconductor diodes device 2
As the only preparation of electronics organic semiconductor diodes device 1, as repeated authentication data.
Embodiment 3
The only preparation of electronics organic semiconductor diodes device 3
As the only preparation of electronics organic semiconductor diodes device 1, as repeated authentication data.
Comparative example 1
The only preparation of electronics organic semiconductor diodes device 4
Method uses conventional commercial compound TmPyPB to make contrast with only as electron transfer layer 40 with embodiment 2
Electronics organic semiconductor diodes device.
Prepared device is in E=1x 106Vcm-1Applied electric field under electron mobility be 1.34x 10-5cm2V-1s-1。
Structural formula described in device
Comparative example 2
The only preparation of electronics organic semiconductor diodes device 5
As the only preparation of electronics organic semiconductor diodes device 4, as repeated authentication data.
Compare the glass transition temperature of material:
Comparator device 1-3 and 4-5 as shown by data material compound 2 is than conventional TmPyPB under identical applied electric field
Electron mobility is higher by 30 times, and glass transition temperature is higher by 3 times, because the glass transition temperature of device lifetime and material has
Close, the glass transition temperature of material is higher, and device stability is better, and the life-span is longer, therefore the material of the present invention is that one kind can answer
High morphological stability in long-life only electronics organic semiconductor diodes device and organic electroluminescence device it is organic
Electron transport material.
Claims (10)
1. high Tg organic electronics transmission apparatus, comprising anode, negative electrode and organic layer, the anode and negative electrode are metal, inorganic matter
Or organic compound；The organic layer has the compound of formula (I) structure,
Wherein, the fluorenes link position of 9,9'- spiral shells two is 1-, 2-, 3-, or 4- position；Wherein, Ar1、Ar2Independently be expressed as it is unsubstituted or
The C6-C25 aryl of person C1-C6 substitutions.
2. according to the high Tg organic electronics transmission apparatus described in claims requirement 1, wherein, Ar1, Ar2Independently it is expressed as
C1-C5 alkyl substitution either phenyl substitution or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,
9- dialkyl group substitute or unsubstituting aromatic yl) fluorenyl or 9,9- it is Spirofluorene-based.
3. according to the high Tg organic electronics transmission apparatus described in claims requirement 2, wherein the fluorenes link position of 9,9'- spiral shell two
For 2- or 4- positions；Wherein, Ar1、Ar2Independently it is expressed as phenyl, tolyl, xylyl, naphthyl, methyl naphthalene, xenyl, two
Phenyl, naphthylphenyl, diphenyl xenyl, (9,9- dialkyl group) fluorenyl, (9,9- dimethyl substitute or unsubstituted phenyl)
Fluorenyl, 9,9- is Spirofluorene-based.
4. according to the high Tg organic electronics transmission apparatus described in claims requirement 3, Ar1、Ar2It is expressed as phenyl.
5. according to the high Tg organic electronics transmission apparatus described in claims requirement 1, the fluorenes link position of 9,9'- spiral shell two is 2-
Or 4- positions；Compound described in formula (I) is having structure compound：
6. require any described high Tg organic electronics transmission apparatus of 1-5, the high Tg organic electronics according to claims
Transmission apparatus is that only electronics organic semiconductor diodes device, the organic layer comprises at least one layer of electron transfer layer；
Or the high Tg organic electronics transmission apparatus is organic electroluminescence device, the organic layer comprises at least one layer and lighted
Layer.
7. according to the high Tg organic electronics transmission apparatus described in claims requirement 6, the luminescent layer is by material of main part
Host-guest system system or single luminescent material system with guest materials composition.
8. according to the high Tg organic electronics transmission apparatus described in claims requirement 6, the organic layer also includes hole and passed
One layer or two layers in defeated layer, electron injecting layer.
9. according to the high Tg organic electronics transmission apparatus described in claims requirement 6, it is hole that the organic layer, which also includes,
Implanted layer, one or more layers in hole blocking layer, hole transmission layer, electron injecting layer.
10. passed according to the high Tg organic electronics transmission apparatus described in claims requirement 9, the hole transmission layer, electronics
Contain the compound described in formula (I) in defeated layer and/or luminescent layer.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610539848.0A CN107586294B (en) | 2016-07-08 | 2016-07-08 | High Tg organic electronic transmission apparatus |
| TW106117614A TWI643856B (en) | 2016-07-08 | 2017-05-26 | High tg organic electronic transmission devices |
| PCT/CN2017/087505 WO2018006679A1 (en) | 2016-07-08 | 2017-06-08 | Organic electronic transport device with high tg |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610539848.0A CN107586294B (en) | 2016-07-08 | 2016-07-08 | High Tg organic electronic transmission apparatus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107586294A true CN107586294A (en) | 2018-01-16 |
| CN107586294B CN107586294B (en) | 2019-10-18 |
Family
ID=60901714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610539848.0A Active CN107586294B (en) | 2016-07-08 | 2016-07-08 | High Tg organic electronic transmission apparatus |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN107586294B (en) |
| TW (1) | TWI643856B (en) |
| WO (1) | WO2018006679A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11233200B2 (en) | 2018-01-16 | 2022-01-25 | Samsung Electronics Co., Ltd. | Condensed cyclic compound, composition including the same, and organic light-emitting device including the condensed cyclic compound |
| CN111490163B (en) * | 2020-04-15 | 2023-09-12 | 电子科技大学 | Perovskite photoelectric detector based on ME-BT composite hole transport layer and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013017189A1 (en) * | 2011-07-29 | 2013-02-07 | Merck Patent Gmbh | Compounds for electronic devices |
| CN103468243A (en) * | 2012-06-06 | 2013-12-25 | 广东阿格蕾雅光电材料有限公司 | Organic electronic materials and organic electroluminescent device |
| JP2014133727A (en) * | 2013-01-11 | 2014-07-24 | Canon Inc | Display device, method of manufacturing display device, and organic compound for use in the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106543172B (en) * | 2015-11-10 | 2019-02-26 | 广东阿格蕾雅光电材料有限公司 | Organic Electron Transport Material |
| CN106549103B (en) * | 2015-11-10 | 2019-05-14 | 广东阿格蕾雅光电材料有限公司 | Only electronics organic semiconductor diodes device |
-
2016
- 2016-07-08 CN CN201610539848.0A patent/CN107586294B/en active Active
-
2017
- 2017-05-26 TW TW106117614A patent/TWI643856B/en active
- 2017-06-08 WO PCT/CN2017/087505 patent/WO2018006679A1/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013017189A1 (en) * | 2011-07-29 | 2013-02-07 | Merck Patent Gmbh | Compounds for electronic devices |
| CN103468243A (en) * | 2012-06-06 | 2013-12-25 | 广东阿格蕾雅光电材料有限公司 | Organic electronic materials and organic electroluminescent device |
| JP2014133727A (en) * | 2013-01-11 | 2014-07-24 | Canon Inc | Display device, method of manufacturing display device, and organic compound for use in the same |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201802090A (en) | 2018-01-16 |
| CN107586294B (en) | 2019-10-18 |
| TWI643856B (en) | 2018-12-11 |
| WO2018006679A1 (en) | 2018-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108352449B (en) | Organic luminescent device | |
| TWI756308B (en) | Hetero-cyclic compound and organic light emitting device using the same | |
| CN105722948B (en) | Heterocyclic compound and use its organic illuminating element | |
| TW201217378A (en) | Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device | |
| CN106164055A (en) | Heterocyclic compound and the organic luminescent device comprising it | |
| TW201242125A (en) | Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device | |
| CN106536527B (en) | Electronics padded coaming and organic electroluminescence device | |
| TW201221618A (en) | Chalcogen-containing aromatic compound, organic semiconductor material, and organic electronic device | |
| CN108884060A (en) | Compound and organic electronic element comprising it | |
| CN109564973A (en) | Organic luminescent device | |
| CN107635973A (en) | Heterocyclic compound and the organic luminescent device for including it | |
| CN110267942A (en) | New heterocyclic compound and the organic luminescent device using it | |
| CN110225909A (en) | New heterocyclic compound and the organic luminescent device comprising it | |
| CN109970670A (en) | Heterocyclic compound and organic luminescent device comprising it | |
| CN110023306A (en) | New heterocyclic compound and the organic luminescent device comprising it | |
| KR20180050122A (en) | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same | |
| CN107778260A (en) | Novel organic luminescent material and the organic illuminating element for including it | |
| CN110234632A (en) | New heterocyclic compound and the organic luminescent device comprising it | |
| CN110177778A (en) | Noval chemical compound and organic luminescent device comprising it | |
| CN109803966A (en) | New compound amine-based and the organic luminescent device using it | |
| CN107586294B (en) | High Tg organic electronic transmission apparatus | |
| WO2020175867A1 (en) | Novel compound and organic light emitting device comprising same | |
| CN108290847A (en) | Noval chemical compound and organic luminescent device comprising it | |
| CN107586295B (en) | High Tg Organic Electron Transport Material | |
| CN106549103B (en) | Only electronics organic semiconductor diodes device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1247190 Country of ref document: HK |
|
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: High Tg organic electron transport devices Effective date of registration: 20201222 Granted publication date: 20191018 Pledgee: Guangdong Nanhai Rural Commercial Bank branch branch of Limited by Share Ltd. Pledgor: GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS Co.,Ltd. Registration number: Y2020980009752 |