CN107586299A - A kind of organic compound and its application using pyridine as core - Google Patents
A kind of organic compound and its application using pyridine as core Download PDFInfo
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 28
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 239000010410 layer Substances 0.000 claims description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 238000005401 electroluminescence Methods 0.000 claims description 14
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012298 atmosphere Substances 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 13
- 229910002027 silica gel Inorganic materials 0.000 claims description 13
- 239000000741 silica gel Substances 0.000 claims description 13
- 229960001866 silicon dioxide Drugs 0.000 claims description 13
- 239000002019 doping agent Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 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
- -1 Asia three Xenyl Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000002346 layers by function Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 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
- 239000000376 reactant Substances 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007772 electrode material Substances 0.000 description 5
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 2
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
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- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 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 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 101100072645 Arabidopsis thaliana IPS3 gene Proteins 0.000 description 1
- NODFGJYBXPEUCQ-UHFFFAOYSA-N CC(C)(CCC1)C1N Chemical compound CC(C)(CCC1)C1N NODFGJYBXPEUCQ-UHFFFAOYSA-N 0.000 description 1
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940126179 compound 72 Drugs 0.000 description 1
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- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 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 1
- 239000012044 organic layer Substances 0.000 description 1
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- 239000010970 precious metal Substances 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a kind of organic compound using pyridine as core and its application, pyridine is A (acceptor in the compound,) group, dibenzo five-ring heterocycles derivative be D (donor) group, form D A or D- π-A structures.The compounds of this invention with it is intermolecular be not easy to crystallize, be not easy to assemble, with good filming the characteristics of, rigid radical in the compounds of this invention molecule can improve the heat endurance of material, the compounds of this invention is applied to OLED as emitting layer material, the OLED produced has good photoelectric properties, can better meet the requirement of panel manufacturing enterprise.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to it is a kind of using pyridine as the compound of core and its as
Application of the emitting layer material on organic electroluminescence device.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for make
New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is quite varied.
OLED luminescent devices just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes collectively constitutes OLED luminescent devices together.
As current device, when the two end electrodes to OLED luminescent devices apply voltage, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, that is, produces OLED electroluminescent.
Organic Light Emitting Diode (OLEDs) large-area flat-plate show and illumination in terms of application cause industrial quarters and
The extensive concern of art circle.However, traditional organic fluorescence materials can only be lighted using 25% singlet exciton to be formed is electrically excited, device
The internal quantum efficiency of part is relatively low (up to 25%).External quantum efficiency is generally less than 5%, also has with the efficiency of phosphorescent devices very big
Gap.Although phosphor material because the strong SO coupling in heavy atom center enhances intersystem crossing, can effectively utilize electricity
The singlet exciton to be formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material is present
Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits its application in OLEDs.Hot activation is prolonged
Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Should
Class material typically has small poor (the △ E of singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing
Lighted into singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior
Quantum efficiency can reach 100%.Meanwhile material structure is controllable, property is stable, cheap without precious metal, in OLEDs
Field has a extensive future.
Although TADF materials can realize 100% exciton utilization rate in theory, following problem there are in fact:(1)
T1 the and S1 states of design molecule have strong CT features, very small S1-T1 state energy gaps, although can be realized by TADF processes
High T1→S1State exciton conversion ratio, but low S1 state radiation transistion speed is also resulted in, consequently it is difficult to have (or realizing) concurrently simultaneously
High exciton utilization rate and high fluorescent radiation efficiency；(2) even if mitigating T exciton concentration quenching effects using doping device, greatly
Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For the actual demand that current OLED shows Lighting Industry, the development of OLED material is also far from enough at present, falls
After the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
The content of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of organic compound using pyridine as core
Thing and its application on organic electroluminescence device.The compounds of this invention is based on TADF mechanism using pyridine as core, as
Emitting layer material is applied to organic electroluminescence device, and the device that the present invention makes has good photoelectric properties, disclosure satisfy that
The requirement of panel manufacturing enterprise.
Technical scheme is as follows：
A kind of organic compound using pyridine as core, shown in the structure such as formula (1) of the organic compound：
In formula (1), Z1~Z6Separately represent nitrogen-atoms or CH；Z1~Z6In have any one or two
It is expressed as nitrogen-atoms；
In formula (1), L represents singly-bound, substituted or unsubstituted C6-60Arlydene, heteroatomic take containing one or more
Generation or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom is nitrogen, oxygen or sulphur；
In formula (1), Ar1、Ar2Expression hydrogen atom, substituted or unsubstituted C independently6-60Aryl, contain one
Or multiple heteroatomic substituted or unsubstituted 5-60 unit's heteroaryls；The hetero atom is nitrogen, oxygen or sulphur；Ar1、Ar2Can be with identical
It is or different；
In formula (1), R1、R2Independently be expressed as hydrogen atom, formula (2) or structure shown in formula (3), and R1、R2
It is asynchronously hydrogen atom；
Wherein, a is expressed asX1、X2、X3、X4Independently be expressed as oxygen atom,
Sulphur atom, selenium atom, C1-10Alkylidene, alkylidene, the alkyl-substituted imines of aryl substitution of straight or branched alkyl substitution
One kind in base or the imido grpup of aryl substitution；A passes through C with formula (1)L1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2
Key, CL‘2-CL’3Key or CL‘3-CL’4Key connection.
The L represents singly-bound, phenylene, biphenylene, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, C1-10Directly
One kind in chain or the alkylidene of branched alkyl substitution；Ar1、Ar2Independently be expressed as hydrogen atom, phenyl, xenyl, three
Xenyl, naphthyl, anthryl, phenanthryl, furyl, thienyl or pyridine radicals；
In the formula (1)Represent any of following structural：
It is describedRepresent any of following structural：
The concrete structure formula of the organic compound is：
Any of.
A kind of organic electroluminescence device containing the organic compound, the organic electroluminescence device are included at least
One one functional layer contains the organic compound using pyridine as core.
A kind of organic electroluminescence device for including the organic compound, using pyridine as core in the luminescent device
Organic compound as luminescent layer material of main part, for making organic electroluminescence device.
A kind of organic electroluminescence device for including the organic compound, using pyridine as core in the luminescent device
Dopant material of the organic compound as luminescent layer, for making organic electroluminescence device.
A kind of method for preparing the organic compound, the reaction equation of methods described are：
The preparation method comprises the following specific steps that：
Weigh with the halogenated compound of pyridine andDissolved with toluene；Add Pd2(dba)3、
Tri-butyl phosphine, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant under the conditions of 95~110 DEG C, reaction
10~24h, is cooled down and filtering reacting solution, filtrate rotate, and is crossed silicagel column, is obtained target product；
The halogenated compound of the pyridine withMol ratio be 1:2.0~3.0, Pd2(dba)3
Mol ratio with the halogenated compound of pyridine is 0.006~0.02:1, the halogenated compound of tri-butyl phosphine and pyridine
Mol ratio is 0.006~0.02:1, the mol ratio of the halogenated compound of sodium tert-butoxide and pyridine is 3.0~5.0:1.
The present invention is beneficial to be had technical effect that：
For the compounds of this invention using nitrogen-containing hetero benzene as parent nucleus, surrounding connects aromatic heterocycle group, destroys the crystallinity of molecule,
Avoid intermolecular aggtegation, be mostly rigid radical, the film forming having had and fluorescence quantum efficiency in molecule, Ke Yizuo
Used for luminescent layer dopant material；The compound structure intramolecular includes electron donor (donor, D) and electron acceptor
The combination of (acceptor, A) can increase Orbital Overlap, improve luminous efficiency, while connect aromatic heterocycle group to obtain
The charge transfer state material that HOMO, LUMO are spatially separating, realizes small S1State and T1Energy level difference (the △ E of statest), so as in Spurs
Reverse intersystem crossing is realized under the conditions of swashing, the use of emitting layer material material of main part is suitable as, further, according to material molecule
The difference of design, such compound can also use as the dopant material of emitting layer material.
Compound of the present invention can be used as emitting layer material to be made applied to OLED luminescent devices, and respectively as hair
Photosphere material of main part or dopant material, good device performance can be obtained, especially includes patent document CN106496198A
In device embodiments be compared as the reference example of the present invention, find the current efficiency of device of the present invention, power efficiency and
External quantum efficiency is greatly improved, for device lifetime lifting clearly.Meanwhile with patent document CN106496198A
In the compound phase ratio enumerated, the structure of the compounds of this invention is simpler, and molecular weight substantially reduces so that such compound
Temperature, which is deposited, to be reduced, and is advantageous to the preparation of device.
Compound-material of the present invention has good application effect in OLED luminescent devices, has good industry
Change prospect.
Brief description of the drawings
Fig. 1 is the device architecture schematic diagram of the compounds of this invention application；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminous
Layer, 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be negative electrode reflection electrode layer；
Fig. 2 is the efficiency curve diagram that device measures at different temperatures.
Embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1：The synthesis of compound 1：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 1,0.025mol raw material B1 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 1, purity
98.1%, yield 63.4%.
Elementary analysis structure (molecular formula C40H25N3O)：Theoretical value C, 85.24；H,4.47；N,7.46；O,2.84；Test
Value：C,85.26；H,4.45；N,7.47；O,2.82.ESI-MS(m/z)(M+)：Theoretical value 563..20, survey molecular weight
563.32。
Embodiment 2：The synthesis of compound 3：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 2,0.025mol raw material B1 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 3, purity
98.3%, yield 63.8%.
Elementary analysis structure (molecular formula C46H29N3O)：Theoretical value C, 86.36；H,4.57；N,6.57；O,2.50；Test
Value：C,86.33；H,4.58；N,6.58；O,2.51.ESI-MS(m/z)(M+)：Theoretical value 639.23, survey molecular weight
639.34。
Embodiment 3：The synthesis of compound 15：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 3,0.025mol raw material B2 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 15, purity
97.7%, yield 62.2%.
Elementary analysis structure (molecular formula C40H25N3O)：Theoretical value C, 85.24；H,4.47；N,7.46；O,2.84；Test
Value：C,85.26；H,4.45；N,7.47；O,2.82.ESI-MS(m/z)(M+)：Theoretical value 563.20, survey molecular weight
563.28。
Embodiment 4：The synthesis of compound 29：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 4,0.025mol B3 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 29, purity
98.7%, yield 62.5%.
Elementary analysis structure (molecular formula C46H29N3O)：Theoretical value C, 86.36；H,4.57；N,6.57；O,2.50；Test
Value：C,86.34；H,4.55；N,6.59；O,2.52.ESI-MS(m/z)(M+)：Theoretical value 639.23, survey molecular weight
639.37。
Embodiment 5：The synthesis of compound 32：
Synthetic route：
With embodiment 3, difference is to replace raw material B2 with raw material B4 the preparation method of compound 32.
Elementary analysis structure (molecular formula C43H31N3)：Theoretical value C, 87.58；H,5.30；N,7.13；Test value：C,
87.57；H,5.27；N,7.14.ESI-MS(m/z)(M+)：Theoretical value 589.25, survey molecular weight 589.33.
Embodiment 6：The synthesis of compound 38：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 5,0.025mol raw material B5 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 38, purity
99.1%, yield 66.4%.
Elementary analysis structure (molecular formula C49H35N3)：Theoretical value C, 88.39；H,5.30；N,6.31；Test value：C,
88.37；H,5.32；N,6.33.ESI-MS(m/z)(M+)：Theoretical value 665.28, survey molecular weight 665.36.
Embodiment 7：The synthesis of compound 44：
Synthetic route：
With embodiment 1, difference is to replace raw material B1 with raw material B6 the preparation method of compound 44.
Elementary analysis structure (molecular formula C42H27N3)：Theoretical value C, 87.93；H,4.74；N,7.32；Test value：C,
87.95；H,4.72；N,7.35.ESI-MS(m/z)(M+)：Theoretical value 573.22, survey molecular weight 573.36.
Embodiment 8：The synthesis of compound 56：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 6,0.025mol raw material B7 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 56, purity
98.3%, yield 63.1%.
Elementary analysis structure (molecular formula C40H25N3O)：Theoretical value C, 85.24；H,4.47；N,7.46；O,2.84；Test
Value：C,85.22；H,4.48；N,7.45；O,2.85.ESI-MS(m/z)(M+)：Theoretical value 563.20, survey molecular weight
563.31。
Embodiment 9：The synthesis of compound 68：
Synthetic route：
With embodiment 8, difference is to replace raw material B7 with raw material B8 the preparation method of compound 68.
Elementary analysis structure (molecular formula C40H25N3O)：Theoretical value C, 85.24；H,4.47；N,7.46；O,2.84.Test
Value：C,85.25；H,4.49；N,7.48；O,2.78.ESI-MS(m/z)(M+)：Theoretical value 563.20, survey molecular weight
563.27。
Embodiment 10：The synthesis of compound 72：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 7,0.025mol raw material B8 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 72, purity
98.3%, yield 63.1%.
Elementary analysis structure (molecular formula C46H29N3O)：Theoretical value C, 86.36；H,4.57；N,6.57；O,2.50；Test
Value：C,86.37；H,4.59；N,6.55；O,2.49.ESI-MS(m/z)(M+)：Theoretical value 639.23, survey molecular weight
639.35。
Embodiment 11：The synthesis of compound 78：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 8,0.025mol raw material B4 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 78, purity
97.8%, yield 64.3%.
Elementary analysis structure (molecular formula C43H31N3)：Theoretical value C, 87.58；H,5.30；N,7.13；Test value：C,
87.59；H,5.32；N,7.11.ESI-MS(m/z)(M+)：Theoretical value 589.25, survey molecular weight 589.36.
Embodiment 12：The synthesis of compound 85：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 9,0.025mol raw material B5 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 85, purity
98.3%, yield 63.1%.
Elementary analysis structure (molecular formula C49H35N3)：Theoretical value C, 88.39；H,5.30；N,6.31；Test value：C,
88.41；H,5.32；N,6.32.ESI-MS(m/z)(M+)：Theoretical value 665.28, survey molecular weight 665.37.
Embodiment 13：The synthesis of compound 94：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 10,0.025mol raw material B9 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 94, purity
99.4%, yield 67.6%.
Elementary analysis structure (molecular formula C49H35N3)：Theoretical value C, 88.39；H,5.30；N,6.31；Test value：C,
88.41；H,5.32；N,6.32.ESI-MS(m/z)(M+)：Theoretical value 665.38, survey molecular weight 665.45.
Embodiment 14：The synthesis of compound 109：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol raw material A 11,0.025mol raw material B7 are added,
0.04mol sodium tert-butoxides, 2 × 10-4mol Pd2(dba)3, 2 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is completely；Natural cooling, filtering, filtrate revolving, silicagel column is crossed, obtains target product 109, purity
98.5%, yield 65.5%.
Elementary analysis structure (molecular formula C41H26N2O)：Theoretical value C, 87.52；H,4.66；N,4.98；O,2.84；Test
Value：C,87.55；H,4.67；N,4.96；O,2.82.ESI-MS(m/z)(M+)：Theoretical value 562.20, survey molecular weight
562.27。
Embodiment 15：The synthesis of compound 132：
Synthetic route：
With embodiment 14, difference is to replace raw material B7 with raw material B4 the preparation method of compound 132.
Elementary analysis structure (molecular formula C44H32N2)：Theoretical value C, 89.76；H,5.48；N,4.76；Test value：C,
89.74；H,5.49；N,4.77.ESI-MS(m/z)(M+)：Theoretical value 588.26, survey molecular weight 588.33.
Embodiment 16：The synthesis of compound 210：
Synthetic route：
With embodiment 14, difference is to replace raw material B7 with raw material B10 the preparation method of compound 132.
Elementary analysis structure (molecular formula C47H28N2O2)：Theoretical value C, 86.48；H,4.32；N,4.29；O,4.90；Test
Value：C,86.45；H,4.34；N,4.28；O,4.93.ESI-MS(m/z)(M+)：Theoretical value 652.22, survey molecular weight
652.31。
The compounds of this invention can use as emitting layer material, to the compounds of this invention 1,3,15,29,32,38,44,
56th, 68,72,78,85,94,109,132,210 and CBP carries out T respectively1The test of energy level, hot property, HOMO energy levels, test knot
Fruit is as shown in table 2.
Table 2
Note：Triplet T1 is the F4600 XRFs test by 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 companies DSC204F1 differential scanning calorimeters)
Measure, 10 DEG C/min of heating rate；Thermal weight loss temperature TdIt is the temperature of the weightlessness 1% in nitrogen atmosphere, in Japanese Shimadzu Corporation
TGA-50H thermogravimetric analyzers on be measured, nitrogen flow 20mL/min；Highest occupied molecular orbital HOMO energy levels be by
Ionizing energy test system (IPS3) is tested, and is tested as atmospheric environment.Control compounds H6, H41, H78 chemical constitution are as follows
It is shown：
As shown in Table 2, the compounds of this invention has higher triplet and higher heat endurance, especially has
Suitable HOMO energy levels.The suitable HOMO energy levels of the compounds of this invention are advantageous to material when OLED is applied between difference film layer
Energy transmission between the injection and transmission in hole and Subjective and Objective material so that using the compounds of this invention as luminescent layer material
The OLED efficiency of material and life-span get a promotion.In addition, the control compounds H6, H41, H78 that include are patent document
Compound in CN106496198A；We have found that the compounds of this invention is compared with control compounds, the chemical constitution of compound
It is simpler, significant decrease of molecular weight, but the glass transition temperature (T of the compounds of this inventiong) and thermal weight loss temperature TdWith contrast
Compound is substantially without significant change.
By the following examples 17~24 and comparative example 1~4 describe the compound that synthesizes of the present invention in detail and make in the devices
For the application effect of luminescent layer material of main part.The comparative example 1~3 included is respectively selected from the implementation in patent CN106496198A
Example 19,22 and 24.Embodiment 18~24 and comparative example 1~4 are compared with embodiment 17, the complete phase of manufacture craft of the device
Together, and identical baseplate material and electrode material are employed, the thickness of electrode material is also consistent, different to device
In the material of main part of luminescent layer 5 convert.The structure composition of each embodiment obtained device is as shown in table 3.Obtained device
Test result is shown in Table 3.
Embodiment 17
(the molybdenum trioxide MoO of 2/ hole injection layer of transparent substrate layer 1/ITO anode layers 33, thickness 10nm) and/hole transmission layer 4
(compound 1 and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5：10 weight is than blending, thickness 30nm)/electricity
Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).Related material
The structural formula of material is as follows：
Specific preparation process is as follows：
Transparent substrate layer 1 is transparent base, such as transparent PI films, glass.Ito anode layer 2 (thickness 150nm) is carried out
Washing, i.e., neutralizing treatment, pure water, drying are carried out successively, then carry out ultraviolet-ozone washing to remove transparent ITO surfaces
Organic residue.On the ito anode layer 2 after having carried out above-mentioned washing, using vacuum deposition apparatus, evaporation thickness is 10nm
Molybdenum trioxide MoO3Used as hole injection layer 3.And then the TAPC of 80nm thickness is deposited as hole transmission layer 4.On
State hole mobile material evaporation terminate after, make OLED luminescent devices luminescent layer 5, its structure include OLED luminescent layers 5 made
By the use of material compound 1 as material of main part, for GD-PACTZ as dopant material, dopant material doping ratio is 10% weight ratio,
Luminescent layer thickness is 30nm.After above-mentioned luminescent layer 5, it is TPBI to continue vacuum evaporation electron transport layer materials.The material
Vacuum evaporation thickness is 40nm, and this layer is electron transfer layer 6.On electron transfer layer 6, by vacuum deposition apparatus, film is made
Thickness is 1nm lithium fluoride (LiF) layer, and this layer is electron injecting layer 7.On electron injecting layer 7, pass through vacuum deposition apparatus, system
Make aluminium (Al) layer that thickness is 80nm, this layer is that negative electrode reflection electrode layer 8 uses.
After completing OLED luminescent devices as described above, anode and negative electrode are connected with known drive circuit, led to
Cross standard method and characterize the OLED, from current/voltage/luminous density characteristic line computation of presentation Lambert emission characteristic, and survey
Measure the life-span.The test result of device is shown in Table 4.
Table 3
Note：It is as shown below to the structure of material of main part used in device luminescent layer 5 in comparative example 1,2,3：
Table 4
Explanation:Device detection performance is used as reference using comparative example 1~4；Current efficiency is in 10mA/cm2Under the conditions of measure；
Life-span test system is owner of the present invention and the OLED life-span tester of Shanghai University's joint research.
The result of table 3 shows：Compound of the present invention can be applied to OLED luminescent devices as luminescent layer material of main part
Make, and compared with comparative example 1~4, either efficiency or life-span obtain larger change than known OLED material, especially
It is the larger lifting of the driving life-span acquisition of device.
By the following examples 25~32 and comparative example 5~8 illustrate the compound that synthesizes of the present invention in the devices as hair
The application effect of photosphere dopant material.The comparative example 5~7 wherein included is respectively selected from the implementation in patent CN106496198A
Example 27,30 and 31.Of the present invention 25~32, the complete phase of manufacture craft of the device compared with embodiment 17 of comparative example 5~8
Together, and identical baseplate material and electrode material are employed, the thickness of electrode material is also consistent, except that device
In luminescent layer 5 in dopant material convert, doping concentration is changed into 7%.The structure composition of each device is as shown in table 5.Institute
The test result for obtaining device is shown in Table 6.
Table 5
Note：The structural formula of dopant material 5 in comparative example, used in 6,7,8 pairs of device luminescent layers 5 is as follows：
Table 6
Explanation:Device detection performance is using comparative example 5~8 as reference, and current efficiency is in 10mA/cm2Under the conditions of measure；
Life-span test system is owner of the present invention and the OLED life-span tester of Shanghai University's joint research.
The result of table 6 shows：Compound of the present invention can be applied to OLED luminescent devices as luminescent layer dopant material
Make, and compared with comparative example 5~8, either efficiency or life-span obtain larger change than known OLED material, especially
It is the larger lifting of the driving life-span acquisition of device.
Work limitation rate is also more stable at low temperature for OLED prepared by further material of the present invention, and device is real
Apply example 23,29 and device comparative example 1,5,8 and carry out efficiency test in -10~80 DEG C of sections, acquired results are as shown in table 7.
Table 7
It was found from the data of table 8, embodiment 23,29 is the device architecture that material of the present invention and known materials are arranged in pairs or groups, and device
Part comparative example 1,5 is compared, and Efficiency at Low Temperature substantially increases, compared with from CBP as the comparative example 8 of material of main part, not only low temperature
Efficiency high, and in temperature elevation process, efficiency steadily raises.
From the point of view of data above application, the compounds of this invention has well as in emitting layer material OLED luminescent devices
Application effect, there is good industrialization prospect.
Although the present invention is disclosed by embodiment and preferred embodiment, it should be appreciated that public the invention is not restricted to institute
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
The scope of attached claim should be consistent with most wide explanation to cover all such modifications and similar arrangement.
Claims (9)
- A kind of 1. organic compound using pyridine as core, it is characterised in that the structure of the organic compound such as formula (1) It is shown：In formula (1), Z1~Z6Separately represent nitrogen-atoms or CH；Z1~Z6In there are any one or two to be expressed as Nitrogen-atoms；In formula (1), L represents singly-bound, substituted or unsubstituted C6-60Arlydene, containing one or more heteroatomic substitutions or Unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom is nitrogen, oxygen or sulphur；In formula (1), Ar1、Ar2Expression hydrogen atom, substituted or unsubstituted C independently6-60Aryl, contain one or more Individual heteroatomic substituted or unsubstituted 5-60 unit's heteroaryls；The hetero atom is nitrogen, oxygen or sulphur；Ar1、Ar2Can be with identical or not Together；In formula (1), R1、R2Independently be expressed as hydrogen atom, formula (2) or structure shown in formula (3), and R1、R2It is different When be hydrogen atom；Wherein, a is expressed asX1、X2、X3、X4Independently to be expressed as oxygen atom, sulphur former Son, selenium atom, C1-10Straight or branched alkyl substitution alkylidene, aryl substitution alkylidene, alkyl-substituted imido grpup or One kind in the imido grpup of aryl substitution；A passes through C with formula (1)L1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key connection.
- 2. organic compound according to claim 1, it is characterised in that L represents singly-bound, phenylene, biphenylene, Asia three Xenyl, naphthylene, anthrylene, phenanthrylene, C1-10One kind in the alkylidene of straight or branched alkyl substitution；Ar1、Ar2Respectively Independent is expressed as hydrogen atom, phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, furyl, thienyl or pyridine radicals.
- 3. organic compound according to claim 1, it is characterised in that in the formula (1)Represent following knot Any of structure formula：
- 4. organic compound according to claim 1, it is characterised in that describedRepresent following knot Any of structure formula：
- 5. organic compound according to claim 1, it is characterised in that the concrete structure formula of the organic compound is：Any of.
- A kind of 6. organic electroluminescence device containing any one of Claims 1 to 5 organic compound, it is characterised in that At least one layer of functional layer that the organic electroluminescence device includes contains the organic compound using pyridine as core.
- A kind of 7. organic electroluminescence device for including any one of the Claims 1 to 5 organic compound, it is characterised in that institute It is the organic compound of core as luminescent layer material of main part to state in luminescent device using pyridine, for making organic electroluminescent Device.
- A kind of 8. organic electroluminescence device for including any one of the Claims 1 to 5 organic compound, it is characterised in that institute State in luminescent device using pyridine be core organic compound as luminescent layer dopant material, for make organic electroluminescence hair Optical device.
- A kind of 9. method for preparing any one of Claims 1 to 5 organic compound, it is characterised in that the reaction of methods described Equation is：The preparation method comprises the following specific steps that：Weigh with the halogenated compound of pyridine andDissolved with toluene；Add Pd2(dba)3, three uncles Butyl phosphine, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant under the conditions of 95~110 DEG C, reaction 10~ 24h, is cooled down and filtering reacting solution, filtrate rotate, and is crossed silicagel column, is obtained target product；The halogenated compound of the pyridine withMol ratio be 1:2.0~3.0, Pd2(dba)3With nitrogen The mol ratio of the halogenated compound of miscellaneous benzene is 0.006~0.02:1, mole of the halogenated compound of tri-butyl phosphine and pyridine Than for 0.006~0.02:1, the mol ratio of the halogenated compound of sodium tert-butoxide and pyridine is 3.0~5.0:1.
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| CN110964007A (en) * | 2018-09-30 | 2020-04-07 | 江苏三月光电科技有限公司 | Compound with quinolinone derivative as core and application of compound in organic electroluminescent device |
| CN110963992A (en) * | 2018-09-30 | 2020-04-07 | 江苏三月光电科技有限公司 | Compound with quinolinone derivative as core and application of compound in organic electroluminescent device |
| CN110964007B (en) * | 2018-09-30 | 2021-10-22 | 江苏三月科技股份有限公司 | Compound with quinolinone derivative as core and application of compound in organic electroluminescent device |
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