CN105732956A - Printable red light emitting polymer and preparing method thereof - Google Patents
Printable red light emitting polymer and preparing method thereof Download PDFInfo
- Publication number
- CN105732956A CN105732956A CN201610231736.9A CN201610231736A CN105732956A CN 105732956 A CN105732956 A CN 105732956A CN 201610231736 A CN201610231736 A CN 201610231736A CN 105732956 A CN105732956 A CN 105732956A
- Authority
- CN
- China
- Prior art keywords
- red
- red light
- emitting polymer
- light emitting
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 9
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 21
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000004044 response Effects 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 26
- 238000007641 inkjet printing Methods 0.000 abstract description 9
- 230000003381 solubilizing effect Effects 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 3
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 abstract 1
- 238000004020 luminiscence type Methods 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000009878 intermolecular interaction Effects 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QYCGHFOTMYKMIY-UHFFFAOYSA-N CC1CC(C2)C2CC1 Chemical compound CC1CC(C2)C2CC1 QYCGHFOTMYKMIY-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/37—Metal complexes
- C08G2261/374—Metal complexes of Os, Ir, Pt, Ru, Rh, Pd
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention relates to a printable red light emitting polymer and a preparing method thereof.The red light emitting polymer is prepared through ring-opening metathesis polymerization, has a norbornene derivative main chain and has red light iridium complex on a side chain.The soft polymer main chain is beneficial for improving viscosity, film-forming performance and flexibility of the material, the material is more suitable for ink jet printed films, and a large-area soft device can be prepared; the red light iridium complex is beneficial for efficient light emitting, while improving material solubility, solubilizing groups can effectively control mutual action among molecules to control annihilation of the triplet state, and light emitting efficiency is improved.The structural formula of the red light emitting polymer is as follow (see the formula in the description).The material has the advantages of being easy to purify, high in yield and heat stability and good in film-forming performance, and a large-area soft device can be prepared through an ink-jet printing method.
Description
Technical field
The invention belongs to photoelectric material and applied technical field, be specifically related to a kind of electroluminescent organic material, more
Relate to one body and can print red-light-emitting polymer and preparation method and application.
Background technology
Organic Light Emitting Diode (OLED) gives large area display and luminaire many advantages, including driving
The switch time etc. that galvanic electricity forces down, efficiency is high, lightweight and shorter.For preparing the material of OLED luminescent layer
Material includes fluorescence and phosphor material.Comparing fluorescent material, OLED based on phosphor material shows higher
Efficiency, this is owing to efficiently altering more between the strong SO coupling permission system of heavy metal, it can be ensured that OLED
Inside can form singletstate and triplet excitons, so that its internal quantum is up to 100%.Another
Aspect, due to the heavy atoms effect of iridium, can make coordination compound produce the strongest Quantum geometrical phase and be conducive to phosphorescence to send out
Penetrate；And, the d orbit splitting in iridium metals ion is relatively big, can avoid the MLCT phase interaction with coordination compound
With, thus improve phosphorescent emissions efficiency.Therefore, complex of iridium is considered as that development OLED has prospect very much
Luminescent material.
The method preparing OLED luminescent layer at present has vapour deposition method and solwution method.Based on little molecule complex of iridium
OLED luminescent layer is mainly prepared by evaporation, and luminescent layer based on dendrimer and polymer is the most logical
Cross solwution method to prepare.Compared to vapour deposition method, solwution method can simplify the structure of large-area OLEDs and reduce into
This.Wherein, inkjet printing once can deposit multiple material, simplifies process step, is more suitable for large-scale production.
But, inkjet printing has the highest requirement to the viscosity of material.And relatively small molecule, polymer possesses preferably
Viscosity, therefore complex of iridium based on polymer is more suitable for inkjet printing masking.
The present invention, by designing the optimization of molecular structure, have developed novel printed red-light-emitting polymer, and
This polymer of successful print on a flexible substrate.This red-light-emitting polymer is to be prepared by ring-opening metathesis polymerization, tool
Norborene is had to derive main chain and be connected with the side chain of complexes of red light iridium.Main polymer chain is conducive to improving material
Viscosity, film property and flexibility, so that material is more suitable for inkjet printing, can realize large area flexible device
Preparation；Complexes of red light iridium contributes to realizing High Efficiency Luminescence, and solubilizing group therein is in the dissolving improving material
While property, it is also possible to the intermolecular interaction of effective control, suppress triplet state-triplet state annihilation, carry
High-luminous-efficiency.
Summary of the invention
Technical problem: the rise of inkjet printing, brings dawn to the large-scale production of OLED.But, spray
Ink prints viscosity and dissolubility for material higher requirement.It is desirable to provide one can print HONGGUANG
Polymer and preparation method thereof, improves the viscosity of luminescent material, dissolubility and the characteristics of luminescence etc., is allowed to applicable
In making large area flexible electronic device by ink jet printing mode.
Technical scheme: the present invention proposes one can print red-light-emitting polymer and preparation method thereof.
This red-light-emitting polymer has norborene and derives on main chain, and its side chain containing complexes of red light iridium, this material
Material polymer represented by following formula I r-P:
Wherein 0≤n≤100, and be natural number, R is selected from following a kind of structure, 1≤m≤10, and m
For natural number,
This red-light-emitting polymer is prepared by ring-opening metathesis polymerization, and its synthetic route is as follows:
The synthesis of Ir-P
Step 1: by complex of iridium presoma Ir-OH, outward-5-norborene-2-carboxylic acid and (N, N-dimethylamino)
Pyridine is put in reaction tube, dissolves dicyclohexylcarbodiimide with dichloromethane and add reaction tube after substituting nitrogen,
Reacting 20-30h under room temperature, question response obtains complex of iridium Ir-M through concentration and chromatography after terminating.
Step 2: first take Grubbs'3rd initiator in glove box in small test tube, dissolve with oxolane
Join to obtain initiator solution, with standby；Then Ir-M is put in reaction tube, after substituting nitrogen, add tetrahydrochysene furan
Mutter, last quickly injection initiator solution in reaction tube, react 1-3h, question response uses vinyl after terminating
Ether cancellation, more concentrated, settle in methanol, sucking filtration obtains polymer Ir-P.
Beneficial effect: the printed red-light-emitting polymer of the present invention possesses following advantage: 1) main polymer chain
Be conducive to improving the viscosity of material, film property, so that material is more suitable for ink jet printing mode masking, can be real
The preparation of existing large area flexible device；2) complexes of red light iridium of side chain contributes to realizing high efficiency luminescence；3)
On side chain, the solubilizing group in complexes of red light iridium is deliquescent it is also possible to effectively control at raising material
Intermolecular interaction, suppresses triplet state-triplet state annihilation, improves luminous efficiency.
Accompanying drawing explanation
Fig. 1 is Ir-M's1H NMR spectra.
Fig. 2 is the MALDI-TOF spectrogram of Ir-M.
Fig. 3 is Ir-P Absorption and emission spectra in dichloromethane solution.
Fig. 4 is the thermogravimetric curve of Ir-P.
Detailed description of the invention
The printed red-light-emitting polymer of the present invention is prepared by ring-opening metathesis polymerization, has norborene derivative main
Chain and the side chain being connected with complexes of red light iridium.Main polymer chain is conducive to improving viscosity and the film property of material, from
And make material be more suitable for ink jet printing mode masking, the preparation of large area flexible device can be realized；HONGGUANG iridium is joined
Compound can realize High Efficiency Luminescence, and solubilizing group therein improving the deliquescent of material it is also possible to
The intermolecular interaction of effective control, suppresses triplet state-triplet state annihilation, improves luminous efficiency.This is red
The general structure of photopolymer is as follows:
Wherein 0≤n≤100, and be natural number, R is selected from following a kind of structure, 1≤m≤10, and m
For natural number,
This red-light-emitting polymer is prepared by ring-opening metathesis polymerization, and its synthetic route is as follows:
Below by way of some embodiments, the present invention will be further described, but embodiment is not intended to containing of the present invention
Scope.
Embodiment 1:
The synthesis of Ir-M
Reaction condition one: by Ir-OH (110mg, 0.072mmol), outer-5-norborene-2-carboxylic acid (12mg,
0.087mmol) put into 10mL reaction tube with (N, N-dimethylamino) pyridine (4.7mg, 0.038mmol)
In, dissolve dicyclohexylcarbodiimide (18.6mg, 0.09mmol) with 2mL dichloromethane after substituting nitrogen
Add reaction tube, under room temperature react 24h, question response terminate after through concentrate and chromatography obtain Ir-M (95mg,
80%).
Reaction condition two: by Ir-OH (100mg, 0.066mmol), outer-5-norborene-2-carboxylic acid (10mg,
0.072mmol) put into 10mL reaction tube with (N, N-dimethylamino) pyridine (4mg, 0.033mmol)
In, dissolve dicyclohexylcarbodiimide (15mg, 0.073mmol) with 1.5mL dichloromethane after substituting nitrogen
Add reaction tube, under room temperature react 20h, question response terminate after through concentrate and chromatography obtain Ir-M (81mg,
75%).
Reaction condition three: by Ir-OH (124mg, 0.081mmol), outer-5-norborene-2-carboxylic acid (17mg,
0.122mmol) put into 10mL reaction tube with (N, N-dimethylamino) pyridine (7mg, 0.057mmol)
In, dissolve dicyclohexylcarbodiimide (25mg, 0.122mmol) with 2.5mL dichloromethane after substituting nitrogen
Adding reaction tube, react 28h under room temperature, question response obtains Ir-M (104 through concentration and chromatography after terminating
Mg, 78%).
1H NMR(400MHz,CDCl3): δ 8.71 (s, 1H), 8.57 (s, 1H), 8.28 (t, J=17.1Hz,
3H), 8.09 (t, J=8.1Hz, 2H), 7.94 (d, J=4.4Hz, 1H), 7.85 7.51 (m, 16H), 7.46
7.29(m,4H),7.24–7.09(m,6H),7.04–6.85(m,6H),6.81–6.72(m,2H),6.68–
6.42 (m, 3H), 6.25 (s, 2H), 6.10 (d, J=18.0Hz, 2H), 4.98 (s, 2H), 3.95 3.63 (m,
6H), 3.02 (dd, J=58.3,39.1Hz, 4H), 2.29 (d, J=17.8Hz, 1H), 2.03 1.68 (m, 3H),
1.34 (d, J=10.7Hz, 16H), 0.98 0.89 (m, 12H).
Embodiment 2:
The synthesis of Ir-P
Reaction condition: first take Grubbs'3rd initiator (6mg, 0.0067mmol) in glove box in 5
In mL small test tube, with 1mL oxolane dissolve join 6.7 × 10-3The initiator solution of mol/L, in case
With；Then Ir-M (110mg, 0.067mmol) is put in 5mL reaction tube, add after substituting nitrogen
0.5mL oxolane, last quickly injection 0.1mL initiator solution in reaction tube, reacts 1.5h, treats
Reaction use vinyl ethyl ether cancellation after terminating, more concentrated, sedimentation in methanol, sucking filtration obtain Ir-P (90mg,
82%).Mole Mw=19297, molecular weight distribution index is 1.59.
Claims (2)
1. one kind can be printed red-light-emitting polymer, it is characterised in that it is derivative main that this red-light-emitting polymer has norborene
Containing complexes of red light iridium on chain, and its side chain, this red-light-emitting polymer is the polymer represented by Ir-P:
Wherein 0≤n≤100, and be natural number, R is selected from following a kind of structure, 1≤m≤10, and m
For natural number,
2. the preparation method that can print red-light-emitting polymer as claimed in claim 1, it is characterised in that should
Method is prepared by ring-opening metathesis polymerization, and its synthetic route is as follows:
The synthesis of Ir-P
Step 1: by complex of iridium presoma (Ir-OH), outer-5-norborene-2-carboxylic acid and (N, N-diformazan
Amino) pyridine puts in reaction tube, and dissolve dicyclohexylcarbodiimide with dichloromethane after substituting nitrogen and add anti-
Ying Guan, reacts 20-30h under room temperature, question response obtains complex of iridium (Ir-M) through concentration and chromatography after terminating；
Step 2: first take Grubbs'3rd initiator in glove box in small test tube, dissolve with oxolane
Join to obtain initiator solution, with standby；Then Ir-M is put in reaction tube, after substituting nitrogen, add tetrahydrochysene furan
Mutter, last quickly injection initiator solution in reaction tube, react 1-3h, question response uses vinyl after terminating
Ether cancellation, more concentrated, settle in methanol, sucking filtration obtains polymer Ir-P.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610231736.9A CN105732956B (en) | 2016-04-14 | 2016-04-14 | A kind of printable red-light-emitting polymer and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610231736.9A CN105732956B (en) | 2016-04-14 | 2016-04-14 | A kind of printable red-light-emitting polymer and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105732956A true CN105732956A (en) | 2016-07-06 |
| CN105732956B CN105732956B (en) | 2018-03-06 |
Family
ID=56255213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610231736.9A Active CN105732956B (en) | 2016-04-14 | 2016-04-14 | A kind of printable red-light-emitting polymer and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105732956B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912313A (en) * | 2018-06-19 | 2018-11-30 | 南京邮电大学 | A kind of printable blue light frequency-doubling and the preparation method and application thereof |
| CN111393615A (en) * | 2020-03-18 | 2020-07-10 | 中国科学院长春应用化学研究所 | Fluorescent high-molecular compound based on polynorbornene main chain and space charge transfer luminescence, preparation method and luminescent device |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004073030A2 (en) * | 2003-02-06 | 2004-08-26 | Georgia Tech Research Corporation | Metal 8-hydroxyquinoline -functionalized polymers and related materials and methods of making and using the same |
| KR20050058879A (en) * | 2003-12-12 | 2005-06-17 | 금호석유화학 주식회사 | A new type of norbornene monomers and polymers for blue light emitting material |
-
2016
- 2016-04-14 CN CN201610231736.9A patent/CN105732956B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004073030A2 (en) * | 2003-02-06 | 2004-08-26 | Georgia Tech Research Corporation | Metal 8-hydroxyquinoline -functionalized polymers and related materials and methods of making and using the same |
| KR20050058879A (en) * | 2003-12-12 | 2005-06-17 | 금호석유화학 주식회사 | A new type of norbornene monomers and polymers for blue light emitting material |
Non-Patent Citations (2)
| Title |
|---|
| CLINTON R.: ""Template-Enhanced Ring-Opening Metathesis Polymerization"", 《MACROMOLECULES》 * |
| SIZHEN CAO ET. AL.: ""Distinct phosphorescence enhancement of red-emitting iridium(III) complexes with formyl-functionalized phenylpyridine ligands"", 《JOURNAL OF MATERIALS CHEMISTRY C》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912313A (en) * | 2018-06-19 | 2018-11-30 | 南京邮电大学 | A kind of printable blue light frequency-doubling and the preparation method and application thereof |
| CN111393615A (en) * | 2020-03-18 | 2020-07-10 | 中国科学院长春应用化学研究所 | Fluorescent high-molecular compound based on polynorbornene main chain and space charge transfer luminescence, preparation method and luminescent device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105732956B (en) | 2018-03-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107827809A (en) | A kind of aromatic amine compound and its organic luminescent device | |
| WO2014031977A1 (en) | Metal compounds and methods and uses thereof | |
| CN112979715B (en) | Metal complex, organic electroluminescent material, organic electroluminescent element, and electroluminescent device | |
| CN104829520B (en) | Electroluminescent organic material and its device prepared using this electroluminescent organic material | |
| CN102977006A (en) | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof | |
| CN112940048B (en) | Metal complex, organic electroluminescent material, organic electroluminescent element, and electroluminescent device | |
| CN109824684B (en) | Spirofluorene derivative organic compound and application thereof in organic electroluminescent device | |
| CN105693631A (en) | Aromatic heterocyclic compound, preparation method thereof and organic electroluminescence device | |
| CN107721907A (en) | A kind of organic compound and its organic luminescent device | |
| CN114773399B (en) | Metal organic luminescent material and application thereof | |
| CN109734608A (en) | A kind of organic compound and its organic electroluminescence device using the compound | |
| CN105732956A (en) | Printable red light emitting polymer and preparing method thereof | |
| CN103739607A (en) | Tri-carbazole multi-arm structural red-light--emitting material and preparation method and application thereof | |
| CN101875674A (en) | Iridium metal complex and application thereof | |
| CN106543123A (en) | A kind of connection anthracene compound and preparation method thereof and organic luminescent device | |
| WO2020237991A1 (en) | Thermally activated delayed fluorescent molecular material, synthesis method therefor, and electroluminescent device | |
| CN110294735B (en) | Compound with anthracene and phenanthrene as core and application of compound in organic electroluminescent device | |
| CN105111143B (en) | A kind of luminous organic material of function admirable and preparation method thereof | |
| CN112979535A (en) | Compound and application thereof | |
| CN111253410A (en) | Compound with fluorene as core and application thereof | |
| CN109734648A (en) | Organic electroluminescence device compound and its organic electroluminescence device for using the compound | |
| CN114790145A (en) | Arylamine compound containing indenofluorene group and organic electroluminescent device | |
| CN103897688A (en) | Organic electroluminescent material and preparation method thereof, and organic electroluminescent device | |
| CN107400085A (en) | A kind of aromatic amine fused ring compound and its organic luminescent device | |
| CN106588592A (en) | Dianthranide derivative, preparation method, and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |