CN109912592A - A kind of compound containing pyridine diindyl and its application on organic electroluminescence device - Google Patents
A kind of compound containing pyridine diindyl and its application on organic electroluminescence device Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 54
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 15
- 239000002346 layers by function Substances 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 194
- 239000002994 raw material Substances 0.000 claims description 75
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- 230000004888 barrier function Effects 0.000 claims description 33
- 230000005540 biological transmission Effects 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 235000019441 ethanol Nutrition 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 17
- -1 9,9- dimethyl fluorenyl Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 239000012043 crude product Substances 0.000 claims description 7
- 238000006392 deoxygenation reaction Methods 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229960001866 silicon dioxide Drugs 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000004653 anthracenylene 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
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 150000005054 naphthyridines Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 165
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 9
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- 238000012360 testing method Methods 0.000 description 26
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- 230000027756 respiratory electron transport chain Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 238000002156 mixing Methods 0.000 description 21
- 238000000921 elemental analysis Methods 0.000 description 15
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 14
- 230000005611 electricity Effects 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 3
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 3
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 3
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 229940127573 compound 38 Drugs 0.000 description 3
- 229940125936 compound 42 Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 101100072645 Arabidopsis thaliana IPS3 gene Proteins 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
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
Abstract
The invention discloses a kind of compound containing pyridine diindyl and its applications on organic electroluminescence device, the compound is made of pyrido indolyl radical, with deep HOMO energy level and hole mobility, it is suitable as hole mobile material or electron-blocking materials；In addition, the compounds of this invention group rigidity is stronger, have the characteristics that it is intermolecular be not easy to crystallize, be not easy to assemble, film forming it is good.After being applied to OLED device as organic electroluminescent functional layer material, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Meanwhile the promotion of device lifetime is clearly.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of compound containing pyridine diindyl and its are having
Application in organic electroluminescence devices.
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
The performances such as service life also need further to be promoted.Proposing high performance research for OLED luminescent device includes: to reduce the driving of device
Voltage improves the luminous efficiency of device, improves the service life etc. of device.In order to realize that the continuous of performance of OLED device mentions
It rises, not only needs the innovation from OLED device structure and manufacture craft, constantly study and create with greater need for oled light sulfate ferroelectric functional material
Newly, the functional material of higher performance OLED is formulated out.Oled light sulfate ferroelectric functional material applied to OLED device can be drawn from purposes
It is divided into two major classes, i.e. charge injection transmission material and luminescent material further can also inject charge into transmission material and be divided into electronics
Transmission material, electron-blocking materials, hole injection transmission material and hole barrier materials are injected, luminescent material can also be divided into
Main body luminescent material and dopant material.In order to make high performance OLED luminescent device, it is desirable that various organic functional materials have
Good photoelectric characteristic, for example, as charge transport materials, it is desirable that there is good carrier mobility, high-vitrification conversion
Temperature etc., the material of main part as luminescent layer require material to have good bipolarity, HOMO/LUMO energy rank appropriate etc..
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 application provide a kind of compound containing pyridine diindyl and its
Application on organic electroluminescence device.The compound of the present invention glass transition temperature with higher and molecule thermal stability close
Suitable HOMO and lumo energy, high hole mobility can effectively improve the luminous efficiency of device after being applied to OLED device production
With the service life of OLED device.
Technical scheme is as follows: a kind of compound containing pyridine diindyl, the structure of the compound such as general formula
(1) shown in:
Wherein, X is expressed as singly-bound；I is equal to 0 or 1；
A is expressed as singly-bound, oxygen atom, C1-10Alkylidene, the alkane of alkylidene, aryl substitution that linear or branched alkyl group replaces
One of the imido grpup that the imido grpup or aryl that base replaces replace；
X1、X2、X3、X4、X5、X6、X7、X8Independently be expressed as C-H or N atom, and the quantity of N atom is 0,1 or 2；
M, n, p, q are equal to 0 or 1；And m+n+p+q >=1；
E is optionally by one or more R1Substituted pyrido indolyl radical；
R1It is expressed as substituted or unsubstituted C6To C30Aryl and substituted or unsubstituted C5To C30One of heteroaryl；
The hetero atom is nitrogen, oxygen or sulphur.
On the basis of above scheme, the present invention can also do following improvement.
Preferably, a kind of compound containing pyridine diindyl, the E can be indicated with general formula (2)；
Wherein, Ar1It is expressed as Dan Jian, substituted or unsubstituted C6-30Arlydene, substituted or unsubstituted C5-30Heteroarylidene
One of；The hetero atom is nitrogen, oxygen or sulphur；
Ar2It is expressed as substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C5-30One of heteroaryl；It is described
Hetero atom is nitrogen, oxygen or sulphur；
Z is expressed as C-H or N atom, and at least one Z indicates N atom.
Preferably, a kind of compound containing pyridine diindyl, in the general formula (1)It indicates are as follows: Any one of.
Preferably, the structure of a kind of compound containing pyridine diindyl, general formula (2) may be expressed as: In appoint
It is a kind of.
Preferably, a kind of compound containing pyridine diindyl, the Ar1It is expressed as singly-bound, phenylene, naphthylene, Asia
Xenyl, anthrylene, furylidene, sub- carbazyl, sub- naphthyridines base, sub- quinolyl, sub- thienyl, sub-pyridyl group, subunit, Asia
One of 9,9- dimethyl fluorenyl, phenanthrylene, sub- dibenzofuran group, sub- dibenzothiophene；
The Ar2It is expressed as phenyl, naphthalene, xenyl, anthryl, furyl, carbazyl, naphthyridines base, quinolyl, thiophene
One of base, pyridyl group, base, 9,9- dimethyl fluorenyl, phenanthryl, dibenzofuran group, dibenzothiophene.
Preferably, a kind of compound containing pyridine diindyl, the concrete structure formula of the compound are as follows:
In appoint
It is a kind of.
The present invention also provides a kind of preparation method of compound containing pyridine diindyl, the preparation method is related to anti-
Answer equation are as follows:
Specific reaction process are as follows:
Raw material A and intermediate M are dissolved in the mixed solution of toluene and ethyl alcohol, Pd (PPh is added after deoxygenation3)4With
K2CO3, under an inert atmosphere 95~110 DEG C of 10~24 hours of reaction, after raw material fully reacting, cooling is filtered, by filtrate
Revolving removes solvent, and crude product crosses silicagel column, obtains target compound；
Wherein, the dosage of the toluene and ethyl alcohol is that every gram of raw material A uses 30~50mL toluene and 5~10mL ethyl alcohol,
The molar ratio of intermediate M and raw material A is 1~3:1, Pd (PPh3)4Molar ratio with raw material A is 0.006~0.03:1, K2CO3With
The molar ratio of raw material A is 1.5~4.5:1.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device includes at least one layer of function
Layer contains a kind of compound containing pyridine diindyl.
Preferably, a kind of organic electroluminescence device, including hole transmission layer/electronic barrier layer, the hole transmission layer/
Electronic barrier layer contains the compound containing pyridine diindyl.
Preferably, a kind of organic electroluminescence device, including luminescent layer, the luminescent layer, which contains, described contains pyrido
The compound of indoles.
The present invention also provides a kind of illumination or display elements, include the organic electroluminescence device.
The present invention is beneficial to be had the technical effect that
The compounds of this invention molecule has asymmetry, avoids intermolecular aggtegation, the compounds of this invention group is rigid
Property it is stronger, have the characteristics that it is intermolecular be not easy to crystallize, be not easy to assemble, have good filming, with high glass transition temperature and
Thermal stability, so, when the compounds of this invention is applied to OLED device, the membranous layer stability after can keeping material filming is improved
OLED device service life.
The compounds of this invention structure balances electrons and holes more in the distribution of luminescent layer, in appropriate HOMO energy level
Under, improve hole injection/transmission performance；Under suitable lumo energy, and play the role of electronic blocking, promotes exciton
Combined efficiency in luminescent layer；When light emitting functional layer materials'use as OLED luminescent device, the collocation of pyridine diindyl this
Branch in invention scope can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduce the efficiency rolling under high current density
Drop reduces device voltage, improves current efficiency and the service life of device.
Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization
Scape.
Detailed description of the invention
Fig. 1 is the structural schematic diagram that material cited by the present invention is applied to OLED device；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transport or electronic blocking
Layer, 5 be luminescent layer, and 6 be electron-transport or hole blocking layer, and 7 be electron injecting layer, and 8 be cathode reflection electrode layer；
Fig. 2 is the curve that current efficiency varies with temperature.
Specific embodiment
Embodiment 1: the synthesis of intermediate M:
(1) raw material B and raw material C are dissolved in the mixed solution of toluene and ethyl alcohol, Pd (PPh is added after deoxygenation3)4With
K2CO3, 95~110 DEG C of 10~24 hours of reaction under an inert atmosphere constantly monitor reaction process with TLC in reaction process, to
After raw material fully reacting, filtrate is rotated and removes solvent by cooling, filtering, and crude product crosses silicagel column, obtains intermediate S；
Wherein, the dosage of the toluene and ethyl alcohol is that every gram of raw material C uses 30~50mL toluene and 5~10mL ethyl alcohol,
The molar ratio of raw material B and raw material C is (1~1.5): 1, Pd (PPh3)4Molar ratio with raw material C is (0.006~0.02): 1,
K2CO3Molar ratio with raw material C is (1.5~2): 1.
(2) under nitrogen protection, it weighs intermediate S 0.01mol to be dissolved in 150mL tetrahydrofuran, is cooled to -78 DEG C, so
The tetrahydrofuran solution of 1.6mol/L n-BuLi is added in backward reaction system, boric acid three is added after 3h is reacted at -78 DEG C
Isopropyl ester reacts 2h, and reaction system is then risen to 0 DEG C, and 10ml 2mol/L hydrochloric acid solution is added, and stirs 3h, fully reacting,
Ether extraction is added, anhydrous magnesium sulfate drying is added in extract liquor, and revolving is recrystallized with alcohol solvent, obtains intermediate M；
Wherein, the molar ratio of the intermediate S and n-BuLi is 1:1~1.5；The intermediate S and three isopropyl of boric acid
The molar ratio of ester is 1:1~1.5.
By taking intermediate M-1 synthesis as an example:
(1) 0.01mol raw material C-1 and 0.012mol raw material B-1 is dissolved in the 150mL (V of toluene and ethyl alcoholToluene: VEthyl alcohol=
5:1) in mixed solution, 0.0002mol Pd (PPh is added after deoxygenation3)4With 0.02mol K2CO3, 110 DEG C under an inert atmosphere
It reacts 24 hours, constantly monitors reaction process with TLC in reaction process, after raw material fully reacting, cooling, filtering will be filtered
Liquid revolving removes solvent, and crude product crosses silicagel column, obtains intermediate S-1；Elemental analysis structure (molecular formula C23H15BrN2): it is theoretical
Value C, 69.19；H,3.79；Br,20.01；N,7.02；Test value: C, 69.23；H,3.82；Br,20.06；N,7.04；ESI-MS
(m/z) (M+): theoretical value 398.04, measured value 398.15.
(2) under nitrogen protection, it weighs intermediate 0.01mol S-1 to be dissolved in 150mL tetrahydrofuran, is cooled to -78 DEG C,
Then the tetrahydrofuran solution of 8ml 1.6mol/L n-BuLi is added into reaction system, is added after reacting 3h at -78 DEG C
0.013mol triisopropyl borate ester reacts 2h, and reaction system is then risen to 0 DEG C, and 10ml 2mol/L hydrochloric acid solution is added, stirs
3h is mixed, ether extraction is added in fully reacting, and anhydrous magnesium sulfate drying is added in extract liquor, and revolving is recrystallized with alcohol solvent, obtained
To intermediate M-1；Elemental analysis structure (molecular formula C23H17BN2O2): theoretical value C, 75.85；H,4.70；B,2.97；N,7.69；
O,8.79；Test value: C, 75.87；H,4.73；B,2.98；N,7.73；O,8.82.ESI-MS(m/z)(M+): theoretical value is
364.14 measured value 364.25.
Intermediate M is prepared with the synthetic method of intermediate M-1, specific structure is as shown in table 1.
Table 1
Embodiment 2: the synthesis of compound 2:
In 250mL there-necked flask, 0.01mol raw material A -1 and 0.012mol raw material B-1 are dissolved in toluene and ethyl alcohol
150mL(VToluene: VEthyl alcohol=5:1) in mixed solution, 0.0002mol Pd (PPh is added after deoxygenation3)4With 0.02mol K2CO3,
Inert atmosphere lower 110 DEG C of 24 hours of reaction constantly monitor reaction process with TLC in reaction process, after raw material fully reacting,
Cooling, filtering, filtrate is rotated and removes solvent, and crude product crosses silicagel column, obtains target product；Elemental analysis structure (molecular formula
C42H28N2): theoretical value C, 89.97；H,5.03；N,5.00；Test value: C, 89.98；H,5.07；N,5.01；ESI-MS(m/z)
(M+): theoretical value 560.23, measured value 560.27.
Embodiment 3: the synthesis of compound 15:
In 250mL there-necked flask, 0.01mol raw material A -2 and 0.012mol raw material B-3 are dissolved in toluene and ethyl alcohol
150mL(VToluene: VEthyl alcohol=5:1) in mixed solution, 0.0002mol Pd (PPh is added after deoxygenation3)4With 0.02mol K2CO3,
Inert atmosphere lower 110 DEG C of 24 hours of reaction constantly monitor reaction process with TLC in reaction process, after raw material fully reacting,
Cooling, filtering, filtrate is rotated and removes solvent, and crude product crosses silicagel column, obtains target product；Elemental analysis structure (molecular formula
C42H28N2): theoretical value C, 89.97；H,5.03；N,5.00；Test value: C, 89.98；H,5.08；N,5.07；ESI-MS(m/z)
(M+): theoretical value 560.23, measured value 560.28.
Embodiment 4: the synthesis of compound 38:
The preparation method of compound 38 is with embodiment 2, the difference is that replacing raw material B-1 with intermediate M-1.Element point
Analyse structure (molecular formula C48H32N2): theoretical value C, 90.54；H,5.07；N,4.40；Test value: C, 90.57；H,5.11；N,
4.43。ESI-MS(m/z)(M+): theoretical value 636.26, measured value 636.27.
Embodiment 5: the synthesis of compound 42:
The preparation method of compound 42, the difference is that replacing raw material A -1 with raw material A -2, uses intermediate with embodiment 2
M-2 replaces raw material B-1.Elemental analysis structure (molecular formula C52H34N2): theoretical value C, 90.93；H,4.99；N,4.08；Test value:
C,90.97；H,5.05；N,4.12.ESI-MS(m/z)(M+): theoretical value 686.27, measured value 686.31.
Embodiment 6: the synthesis of compound 58:
The preparation method of compound 58 is with embodiment 2, the difference is that replacing raw material A -1 with raw material A -3.Elemental analysis
Structure (molecular formula C42H28N2): theoretical value C, 89.97；H,5.03；N,5.00；Test value: C, 90.01；H,5.06；N,5.03.
ESI-MS(m/z)(M+): theoretical value 560.23, measured value 560.27.
Embodiment 7: the synthesis of compound 64:
The preparation method of compound 64 is with embodiment 2, the difference is that raw material A -1 is replaced with raw material A -4, with raw material B-
4 replacement raw material B-1.Elemental analysis structure (molecular formula C42H28N2): theoretical value C, 89.97；H,5.03；N,5.00；Test value: C,
90.03；H,5.07；N,5.02.ESI-MS(m/z)(M+): theoretical value 560.23, measured value 560.29.
Embodiment 8: the synthesis of compound 70:
The preparation method of compound 70, the difference is that replacing raw material A -1 with raw material A -4, uses intermediate with embodiment 2
M-1 replaces raw material B-1.Elemental analysis structure (molecular formula C48H32N2): theoretical value C, 90.54；H,5.07；N,4.40；Test value:
C,90.57；H,5.11；N,4.48.ESI-MS(m/z)(M+): theoretical value 636.26, measured value 636.31.
Embodiment 9: the synthesis of compound 98:
The preparation method of compound 98, the difference is that replacing raw material A -1 with raw material A -4, uses intermediate with embodiment 2
M-2 replaces raw material B-1.Elemental analysis structure (molecular formula C54H34N2): theoretical value C, 90.93；H,4.99；N,4.08；Test value:
C,90.97；H,5.03；N,4.13.ESI-MS(m/z)(M+): theoretical value 686.27, measured value 686.31.
Embodiment 10: the synthesis of compound 102:
In 250mL there-necked flask, 0.01mol raw material A -5 and 0.012mol raw material B-1 are dissolved in toluene and ethyl alcohol
150mL(VToluene: VEthyl alcohol=5:1) in mixed solution, 0.0002mol Pd (PPh is added after deoxygenation3)4With 0.02mol K2CO3,
Inert atmosphere lower 110 DEG C of 24 hours of reaction constantly monitor reaction process with TLC in reaction process, after raw material fully reacting,
Cooling, filtering, filtrate is rotated and removes solvent, and crude product crosses silicagel column, obtains target product；Elemental analysis structure (molecular formula
C42H26N2): theoretical value C, 90.29；H,4.69；N,5.01；Test value: C, 92.31；H,4.74；N,5.08.ESI-MS(m/z)
(M+): theoretical value 558.21, measured value 558.27.
Embodiment 11: the synthesis of compound 134:
The preparation method is the same as that of Example 10 for compound 134, the difference is that changing raw material A -5 with raw material A -6, uses intermediate
M-1 replaces raw material B-1.Elemental analysis structure (molecular formula C48H30N2): theoretical value C, 90.82；H,4.76；N,4.41；Test value:
C,90.85；H,4.79；N,4.44.ESI-MS(m/z)(M+): theoretical value 634.24, measured value 634.27.
Embodiment 12: the synthesis of compound 140:
The preparation method is the same as that of Example 10 for compound 140, the difference is that replacing raw material B-1 with intermediate M-3.Element
Analyze structure (molecular formula C51H31N3): theoretical value C, 89.32；H,4.56；N,6.13；Test value: C, 89.34；H,4.59；N,
6.17。ESI-MS(m/z)(M+): theoretical value 685.25, measured value 685.31.
Embodiment 13: the synthesis of compound 143:
The preparation method is the same as that of Example 10 for compound 143, the difference is that replacing raw material A -5 with raw material A -7.Element point
Analyse structure (molecular formula C45H32N2): theoretical value C, 89.97；H,5.37；N,4.66；Test value: C, 90.02；H,5.41；N,
4.69。ESI-MS(m/z)(M+): theoretical value 600.26, measured value 600.32.
Embodiment 14: the synthesis of compound 155:
The preparation method is the same as that of Example 10 for compound 155, the difference is that replacing raw material A -5 with raw material A -8.Element point
Analyse structure (molecular formula C45H32N2): theoretical value C, 89.97；H,5.37；N,4.66；Test value: C, 90.01；H,5.43；N,
4.69。ESI-MS(m/z)(M+): theoretical value 600.26, measured value 600.33.
Embodiment 15: the synthesis of compound 182:
The preparation method is the same as that of Example 10 for compound 182, the difference is that raw material A -5 is replaced with raw material A -8, with centre
Body M-4 replaces raw material B-1.Elemental analysis structure (molecular formula C51H36N2): theoretical value C, 90.50；H,5.36；N,4.14；Test
Value: C, 90.54；H,5.38；N,4.17.ESI-MS(m/z)(M+): theoretical value 676.29, measured value 676.32.
Embodiment 16: the synthesis of compound 197:
The preparation method of compound 197 is with embodiment 2, the difference is that replacing raw material A -1 with raw material A -9.Element point
Analyse structure (molecular formula C42H28N2O): theoretical value C, 87.47；H,4.89；N,4.86；O,2.77；Test value: C, 87.55；H,
4.93；N,4.88；O,2.81.ESI-MS(m/z)(M+): theoretical value 576.22, measured value 576.31.
Embodiment 17: the synthesis of compound 199:
The preparation method of compound 199 is with embodiment 2, the difference is that replacing raw material A -1 with raw material A -10.Element point
Analyse structure (molecular formula C42H28N2O): theoretical value C, 87.47；H,4.89；N,4.86；O,2.77；Test value: C, 87.54；H,
4.93；N,4.88；O,2.79.ESI-MS(m/z)(M+): theoretical value 576.22, measured value 576.28.
Embodiment 18: the synthesis of compound 201:
201 preparation method of compound is with embodiment 2, the difference is that replacing raw material A -1 with raw material A -11.Elemental analysis
Structure (molecular formula C45H34N2): theoretical value C, 89.67；H,5.69；N,4.65；Test value: C, 89.69；H,5.71；N,4.68.
ESI-MS(m/z)(M+): theoretical value 602.27, measured value 602.29.
Embodiment 19: the synthesis of compound 215:
The preparation method is the same as that of Example 10 for compound 215, the difference is that replacing raw material A -5 with raw material A -12.Element point
Analyse structure (molecular formula C41H25N3): theoretical value C, 87.99；H,4.50；N,7.51；Test value: C, 88.05；H,4.53；N,
7.54。ESI-MS(m/z)(M+): theoretical value 559.20, measured value 559.26.
Embodiment 20: the synthesis of compound 223:
The preparation method is the same as that of Example 10 for compound 223, the difference is that raw material A -5 is replaced with raw material A -13, in
Mesosome M-2 replaces raw material B-1.Elemental analysis structure (molecular formula C51H31N3): theoretical value C, 89.32；H,4.56；N,6.13；It surveys
Examination value: C, 89.34；H,4.62；N,6.15.ESI-MS(m/z)(M+): theoretical value 685.25, measured value 685.31.
Embodiment 21: the synthesis of compound 234:
The preparation method is the same as that of Example 10 for compound 234, the difference is that replacing raw material A -5 with raw material A -14.Element
Analyze structure (molecular formula C40H24N4): theoretical value C, 85.69；H,4.31；N,9.99；Test value: C, 85.73；H,4.33；N,
10.03。ESI-MS(m/z)(M+): theoretical value 560.20, measured value 560.04.
Embodiment 22: the synthesis of compound 243:
The preparation method is the same as that of Example 10 for compound 243, the difference is that raw material A -5 is replaced with raw material A -14, in
Mesosome M-5 replaces raw material B-1.Elemental analysis structure (molecular formula C52H32N4): theoretical value C, 87.62；H,4.52；N,7.86；It surveys
Examination value: C, 87.65；H,4.55；N,7.89.ESI-MS(m/z)(M+): theoretical value 712.26, measured value 712.31.
This organic compound uses in luminescent device, has high Tg (glass transition temperature) temperature and triplet
(T1), suitable HOMO, lumo energy can be used as hole barrier/electron transport material and use, and also can be used as emitting layer material makes
With.Hot property, T1 energy level and the test of HOMO energy level are carried out respectively to the compounds of this invention and current material, as a result such as 2 institute of table
Show.
Table 2
Note: triplet T1 is tested by the F4600 Fluorescence Spectrometer of Hitachi, and the test condition of material is 2*10-5's
Toluene solution；Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimeter)
Measurement, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in Japanese Shimadzu Corporation
TGA-50H thermogravimetric analyzer on be measured, nitrogen flow 20mL/min；Highest occupied molecular orbital HOMO energy level be by
Ionizing energy test macro (IPS3) test, is tested as atmospheric environment.
By upper table data it is found that CBP the and TPBi material that comparison is applied at present, organic compound of the invention have high
Glass transition temperature can be improved material membrane phase stability, further increase device service life；With high triplet state energy
Grade, can stop luminescent layer energy loss, to promote device light emitting efficiency.Material of the present invention and application material have phase simultaneously
As HOMO energy level.Therefore, the present invention contains the organic material of pyridine diindyl in the different function layer for being applied to OLED device
Afterwards, the luminous efficiency and service life of device can be effectively improved.
Below by way of device embodiments 1~21 and device comparative example 1 OLED material that the present invention will be described in detail synthesizes in device
Application effect in part.Device embodiments 2~21 of the present invention, the device compared with device embodiments 1 of device comparative example 1
Manufacture craft it is identical, and use identical baseplate material and electrode material, the film thickness of electrode material is also kept
Unanimously, except that the emitting layer material in 2~13 pairs of devices of device embodiments converts；14~21 pairs of device embodiments
Hole barrier/electron transport layer materials of device convert, the performance test results of each embodiment obtained device such as 3 institute of table
Show.
Device embodiments 1:
As shown in Figure 1, a kind of electroluminescent device, preparation step includes: ITO sun a) cleaned on transparent substrate layer 1
Pole layer 2 is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, 2 points is then handled in plasma cleaner
Clock；B) on ito anode layer 2, hole injection layer material HAT-CN is deposited by vacuum evaporation mode, with a thickness of 10nm, this layer
As hole injection layer 3；C) on hole injection layer 3, hole mobile material NPB is deposited by vacuum evaporation mode, with a thickness of
80nm, the layer are hole transmission layer/electronic barrier layer 4；D) luminescent layer 5 is deposited on hole transport/electronic barrier layer 4, it is main
Body material is the compounds of this invention 2 and compound GH, and dopant material is Ir (ppy)3, compound 2, GH and Ir (ppy)3Three's matter
Amount is than being 50:50:10, with a thickness of 40nm；E) on luminescent layer 5, electron transport material is deposited by vacuum evaporation mode
TPBI, with a thickness of 35nm, this layer of organic material is used as hole barrier/electron transfer layer 6；F) it is passed in hole barrier/electronics
On defeated layer 6, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electron injecting layer 7；G) electron injecting layer 7 it
On, vacuum evaporation cathode Al (100nm), the layer is cathode reflection electrode layer 8；Electroluminescent device is completed according to above-mentioned steps
After production, the driving voltage of measurement device, current efficiency, the result is shown in shown in table 3.The following institute of the molecular machinery formula of associated materials
Show:
Device embodiments 2:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 15, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 3:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 38, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 4:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: compound 42 and Ir (ppy)3
Constituted by weight 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 5:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 58, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 6:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 64, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 7:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: compound 70 and Ir (ppy)3
Constituted by weight 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 8:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 98, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 9:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 102 and Ir of/luminescent layer 5
(ppy)3Constituted by weight 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electronics note
Enter layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 10:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 134, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 11:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 197, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 12:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 199, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 13:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB) (thickness: 40nm, material: compound 201, GH and Ir of/luminescent layer 5
(ppy)3Constituted by weight 50:50:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electricity
Sub- implanted layer 7 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 14:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 140)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 15:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 143)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 16:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 155)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 17:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 182)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 18:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 215)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 19:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 223)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 20:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 234)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 21:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: compound 243)/electron injecting layer 7
(thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device comparative example 1:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 80nm, material: NPB)/luminescent layer 5 (thickness: 40nm, material: CBP and Ir (ppy)3By weight
Amount is constituted than 90:10 blending)/hole barrier/electron transfer layer 6 (thickness: 35nm, material: TPBI)/electron injecting layer 7 (thickness
Degree: 1nm, material: LiF)/Al (thickness: 100nm).The detection data of gained electroluminescent device is shown in Table 3.
Table 3
By the result of table 3 can be seen that organic compound of the present invention can be applied to OLED luminescent device production, and with than
It is compared compared with example, either efficiency or service life obtain larger change, the especially service life of device than known OLED material
Obtain biggish promotion.
Work limitation rate is also more stable at low temperature for the OLED device of further material preparation of the present invention, by device reality
It applies example 2,9,17 and device comparative example 1 and carries out efficiency test in -10~80 DEG C of sections, acquired results are as shown in table 4 and Fig. 2.
Table 4
From the data of table 4 and Fig. 2 it is found that device embodiments 2,9,17 are material of the present invention and the device that known materials are arranged in pairs or groups
Structure is compared with device comparative example 1, and not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency is steadily increased.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (11)
1. a kind of compound containing pyridine diindyl, which is characterized in that shown in the structure of the compound such as general formula (1):
Wherein, X is expressed as singly-bound；I is equal to 0 or 1；
A is expressed as singly-bound, oxygen atom, C1-10Alkylidene, the alkyl of alkylidene, aryl substitution that linear or branched alkyl group replaces take
One of the imido grpup that the imido grpup or aryl in generation replace；
X1、X2、X3、X4、X5、X6、X7、X8Independently be expressed as C-H or N atom, and the quantity of N atom is 0,1 or 2；
M, n, p, q are equal to 0 or 1；And m+n+p+q >=1；
E is optionally by one or more R1Substituted pyrido indolyl radical；
R1It is expressed as substituted or unsubstituted C6To C30Aryl and substituted or unsubstituted C5To C30One of heteroaryl；It is described
Hetero atom is nitrogen, oxygen or sulphur.
2. a kind of compound containing pyridine diindyl according to claim 1, which is characterized in that the E can use general formula
(2) it indicates；
Wherein, Ar1It is expressed as Dan Jian, substituted or unsubstituted C6-30Arlydene, substituted or unsubstituted C5-30In heteroarylidene
It is a kind of；The hetero atom is nitrogen, oxygen or sulphur；
Ar2It is expressed as substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C5-30One of heteroaryl；The miscellaneous original
Son is nitrogen, oxygen or sulphur；
Z is expressed as C-H or N atom, and at least one Z indicates N atom.
3. a kind of compound containing pyridine diindyl according to claim 1, which is characterized in that in the general formula (1)It indicates are as follows:
Any one of.
4. a kind of compound containing pyridine diindyl according to claim 2, which is characterized in that the structure of general formula (2)
It may be expressed as:
Any one of.
5. a kind of compound containing pyridine diindyl according to claim 2, which is characterized in that the Ar1It is expressed as list
Key, phenylene, naphthylene, biphenylene, anthrylene, furylidene, sub- carbazyl, sub- naphthyridines base, sub- quinolyl, sub- thiophene
Base, sub-pyridyl group, subunit, Asia 9,9- dimethyl fluorenyl, phenanthrylene, sub- dibenzofuran group, in sub- dibenzothiophene
It is a kind of；
The Ar2It is expressed as phenyl, naphthalene, xenyl, anthryl, furyl, carbazyl, naphthyridines base, quinolyl, thienyl, pyridine
One of base, base, 9,9- dimethyl fluorenyl, phenanthryl, dibenzofuran group, dibenzothiophene.
6. a kind of compound containing pyridine diindyl according to claim 1, which is characterized in that the tool of the compound
Body structural formula are as follows:
In appoint
It is a kind of.
7. a kind of a kind of preparation method of the compound containing pyridine diindyl as described in any one of claims 1 to 6, special
Sign is, the reaction equation that the preparation method is related to are as follows:
Specific reaction process are as follows:
Raw material A and intermediate M are dissolved in the mixed solution of toluene and ethyl alcohol, Pd (PPh is added after deoxygenation3)4And K2CO3,
95~110 DEG C of 10~24 hours of reaction under inert atmosphere, after raw material fully reacting, filtrate is rotated and is removed by cooling, filtering
Solvent, crude product cross silicagel column, obtain target compound；
Wherein, the dosage of the toluene and ethyl alcohol is that every gram of raw material A uses 30~50mL toluene and 5~10mL ethyl alcohol, intermediate
The molar ratio of body M and raw material A is 1~3:1, Pd (PPh3)4Molar ratio with raw material A is 0.006~0.03:1, K2CO3With raw material
The molar ratio of A is 1.5~4.5:1.
8. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes at least one layer of functional layer
Contain the compound described in any one of claims 1-6 containing pyridine diindyl.
9. organic electroluminescence device according to claim 8, including hole transmission layer/electronic barrier layer, feature exist
In the hole transmission layer/electronic barrier layer contains the chemical combination described in any one of claims 1-6 containing pyridine diindyl
Object.
10. organic electroluminescence device according to claim 8, including luminescent layer, which is characterized in that the luminescent layer contains
Have the right to require 1-6 described in any item the compound containing pyridine diindyl.
11. a kind of illumination or display element, which is characterized in that include any organic electroluminescence of claim 8-10
Part.
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| CN112574045A (en) * | 2020-12-08 | 2021-03-30 | 武汉华星光电半导体显示技术有限公司 | Hole transport material, preparation method thereof and electroluminescent device |
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