CN109053813A - A kind of feux rouges metal complex, preparation method and application - Google Patents
A kind of feux rouges metal complex, preparation method and application Download PDFInfo
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- CN109053813A CN109053813A CN201810880427.3A CN201810880427A CN109053813A CN 109053813 A CN109053813 A CN 109053813A CN 201810880427 A CN201810880427 A CN 201810880427A CN 109053813 A CN109053813 A CN 109053813A
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000003446 ligand Substances 0.000 claims abstract description 51
- 239000000463 material Substances 0.000 claims abstract description 20
- 238000004821 distillation Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
- 238000004440 column chromatography Methods 0.000 claims description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 22
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 19
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 19
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 229910052741 iridium Inorganic materials 0.000 claims description 16
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims description 5
- LHVXEBCEDNAZPX-UHFFFAOYSA-N 2-phenyl-1,5-naphthyridine Chemical compound C1=CC=CC=C1C1=CC=C(N=CC=C2)C2=N1 LHVXEBCEDNAZPX-UHFFFAOYSA-N 0.000 claims description 3
- ZPEFNZXLUHZKQQ-UHFFFAOYSA-N 2-phenylpyrido[3,2-d]pyrimidine Chemical compound C1=CC=CC=C1C1=NC=C(N=CC=C2)C2=N1 ZPEFNZXLUHZKQQ-UHFFFAOYSA-N 0.000 claims description 3
- VDDAVZWCRBHDLQ-UHFFFAOYSA-N 2-phenylquinazoline Chemical compound C1=CC=CC=C1C1=NC=C(C=CC=C2)C2=N1 VDDAVZWCRBHDLQ-UHFFFAOYSA-N 0.000 claims description 3
- AJUMVVYEUXGKQU-UHFFFAOYSA-N 3-phenylcinnoline Chemical compound C1=CC=CC=C1C1=CC2=CC=CC=C2N=N1 AJUMVVYEUXGKQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 15
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- NGIFHAUKQGDVSR-UHFFFAOYSA-N 6,7-dimethoxy-1-(3,4,5-triethoxyphenyl)isoquinoline Chemical class CCOC1=C(OCC)C(OCC)=CC(C=2C3=CC(OC)=C(OC)C=C3C=CN=2)=C1 NGIFHAUKQGDVSR-UHFFFAOYSA-N 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 229950003545 octaverine Drugs 0.000 abstract 1
- 230000003335 steric effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 8
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 3
- -1 saturated aliphatic radical Chemical class 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- TYONHSPZXLFWKI-UHFFFAOYSA-N (2,4-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C(C)=C1 TYONHSPZXLFWKI-UHFFFAOYSA-N 0.000 description 1
- OOMZKLJLVGQZGV-UHFFFAOYSA-N (2,5-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(C)C(B(O)O)=C1 OOMZKLJLVGQZGV-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- KDVZJKOYSOFXRV-UHFFFAOYSA-N (3,4-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1C KDVZJKOYSOFXRV-UHFFFAOYSA-N 0.000 description 1
- DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 1
- BJQCPCFFYBKRLM-UHFFFAOYSA-N (3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 1
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001768 cations Chemical class 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
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
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- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to field of organic electroluminescent materials, disclose a kind of feux rouges metal complex, preparation method and its application formed by alkyl-substituted octaverine as main ligand.The present invention introduces different alkyl substituents on main ligand, and it, to effectively reduce the use cost of material, is extremely advantageous to industrialized production that the purifying and distillation yield for material, which have, which to be significantly improved,.Simultaneously as the space steric effect of increased alkyl chain, the steric hindrance enhancing of molecule improves luminous efficiency so that luminescence queenching situation mitigates.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and particularly relates to a red light metal complex, and a preparation method and application thereof.
Background
in recent years, a great deal of research shows that iridium complexes are considered to be the most ideal choice for OLEDs (organic electroluminescent devices) phosphorescent materials among numerous heavy metal element complexes, iridium atoms with an outer electronic structure of 5d76s2 have a 5d6 electronic configuration after forming + 3-valent cations, have a stable hexa-coordinated octahedral structure, and enable the materials to have high chemical stability and thermal stability, and meanwhile, Ir (III) has a large spin-orbit coupling constant (ξ ═ 3909cm < -1 >) which is beneficial to improving the internal quantum yield of the complexes and reducing the luminescence life, thereby improving the overall performance of the luminescent devices.
As a phosphorescent material, the iridium complex generally has a microsecond order, and easily causes phosphorescence quenching between a triplet-triplet state and a triplet-exciton of the iridium complex. In addition, in the current commonly used materials, the hole mobility of the hole transport material is much higher than the electron mobility of the electron transport material, and the commonly used host material is mainly used for hole transport, which results in the accumulation of a large amount of excess holes at the interface of the light emitting layer and the electron transport layer. Both of these factors result in reduced efficiency and severe efficiency roll-off. Researches show that if the iridium complex has higher electron transmission capability, the iridium complex can effectively increase the transmission and distribution of electrons in a light-emitting layer, widen an electron-hole region and balance the number of electron-hole pairs, greatly improve the efficiency of a device and reduce the roll-off of the efficiency.
CN106432346A discloses an iridium complex, a preparation method thereof and an electroluminescent device using the iridium complex, which comprises two main ligands and an auxiliary ligand, wherein the main ligands are 2- (4, 6-ditrifluoromethylpyridine-3-) quinoline, 2- (4, 6-ditrifluoromethylpyridine-4-) quinoline, 2- (4, 6-ditrifluoromethylpyridine-3-) isoquinoline, 2- (4, 6-ditrifluoromethylpyridine-4-) isoquinoline, 2- (4, 6-ditrifluoromethylpyridine-3-) quinazoline, 2- (4, 6-ditrifluoromethylpyridine-4-) quinazoline, 2- (4, 6-ditrifluoromethylpyridine-3-) phthalazine, 2- (4, 6-bis (trifluoromethyl) pyridine-4-) phthalazine derivative, wherein the auxiliary ligand is acetylacetone or dibenzoylmethane, namely the patent only protects the metal complex with two auxiliary ligand structures. However, the performances of the complex in sublimation yield and luminous efficiency are not satisfactory enough, and a great promotion space is provided.
Disclosure of Invention
The invention aims to provide a red light metal complex formed by taking alkyl substituted phenyl isoquinoline derivative as a main ligand.
Another object of the present invention is to provide a process for preparing the above red-emitting metal complex.
The invention also aims to provide application of the red-light metal complex.
The purpose of the invention is realized by the following technical scheme:
embodiments of the present invention provide a red-emitting metal complex having a structure represented by general formula (I):
wherein,
R1、R2、R3and R4Each independently is a substituted or unsubstituted C1-C12 alkyl group;
m is a metal atom selected from the group consisting of a group VIII metal element, a group IB metal element, a group IA metal element, and a group IIA metal element;
a is a nitrogen-containing heterocycle, B is an aromatic ring or a heterocycle; ring structure a and at least one ring structure B are fused to adjacent ring structures at any position;
m is 2 or 3, n is 1 or 0;
l is an auxiliary ligand.
Preferably, L is a bidentate ligand.
Further preferably, L is a Tpip ligand as shown below, and M is Ir, M is 2:
preferably, the red light metal complex provided by the embodiment of the present invention has a structure represented by a general formula (II):
wherein,
R1、R2、R3and R4Each independently is a substituted or unsubstituted C1-C12 alkyl group;
a is a nitrogen-containing heterocycle, B is an aromatic ring or a heterocycle;
ring structure a and at least one ring structure B are fused to adjacent ring structures at any position.
Preferably, the fused structure of ring a and ring B is selected from the following:
10. preferably, the red-light metal complex provided by the embodiment of the present invention has a structure selected from one of the following structures:
unless otherwise indicated, the following terms used in the specification and claims have the meanings discussed below:
"alkyl" means a saturated aliphatic radical of 1 to 20 carbon atoms, including straight and branched chain radicals (a numerical range referred to herein, e.g., "1 to 20", means that the radical, in this case alkyl, may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms). Preferably, the alkyl group is a medium size alkyl group having 1 to 10 carbon atoms, and more preferably, the alkyl group is an alkyl group having 1 to 8 carbon atoms, such as methyl, ethyl, propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, pentyl, etc.
An "aromatic ring" means an all-carbon monocyclic or fused polycyclic group of 6 to 12 carbon atoms having a completely conjugated pi-electron system. Non-limiting examples of aryl groups are phenyl, naphthyl and anthracenyl.
"heterocycle" means a monocyclic or fused ring group of 5 to 12 ring atoms containing one, two, three or four ring heteroatoms selected from N, O or S, the remaining ring atoms being C, and additionally having or not having a completely conjugated pi-electron system.
Embodiments of the present invention also provide a method for preparing the above-described red-emitting metal complex, which is synthesized via the following general synthetic route: mixing an iridium dimeric bridged complex containing two main ligands, a tetraphenylphosphonimide auxiliary ligand and sodium carbonate, wherein the main ligand is any one of phenylisoquinoline, phenylbenzopyridazine, phenylbenzopyrimidine, phenylpyridopyridine and phenylpyridopyrimidine; adding a 2-ethoxyethanol solution, carrying out heating reaction at 120-140 ℃, reacting for 12-48 h, cooling to room temperature, carrying out reduced pressure distillation to remove the solvent, extracting with dichloromethane, concentrating, carrying out column chromatography separation to obtain a crude product of the complex, and sublimating to obtain the pure iridium complex.
The embodiment of the invention also provides application of the red light metal complex in organic electroluminescent materials.
In the technical scheme of the application, the iridium complex formed by the alkyl-substituted phenylisoquinoline derivative is provided, different alkyl substituents are introduced on the main ligand, the purification and sublimation yield of the material are obviously improved, the use cost of the material is reduced, and the iridium complex is very favorable for industrial production. Meanwhile, due to the steric hindrance effect of the added alkyl chain, the steric hindrance of molecules is enhanced, so that the luminescence quenching condition is reduced, and the luminescence efficiency is improved.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention will be described in detail with reference to the following examples. However, it will be appreciated by those of ordinary skill in the art that numerous technical details are set forth in order to provide a better understanding of the present invention in its various embodiments. However, the technical solutions claimed in the claims of the present invention can be implemented without these technical details and with various changes and modifications based on the following embodiments. Compound (I)
In some embodiments of the present invention, there is provided a red-emitting metal complex having a structure represented by general formula (I):
wherein,
R1、R2、R3and R4Each independently is a substituted or unsubstituted C1-C12 alkyl group;
m is a metal atom selected from the group consisting of a group VIII metal element, a group IB metal element, a group IA metal element, and a group IIA metal element;
a is a nitrogen-containing heterocycle, B is an aromatic ring or a heterocycle;
ring structure a and at least one ring structure B are fused to adjacent ring structures at any position;
m is 2 or 3, n is 1 or 0;
l is an auxiliary ligand.
In some embodiments of the invention, L is a bidentate ligand.
In some embodiments of the invention, L is a Tpip ligand as shown below, and M is Ir, M is 2:
in some embodiments of the present invention, red-emitting metal complexes are provided having a structure represented by formula (II):
wherein,
R1、R2、R3and R4Each independently is a substituted or unsubstituted C1-C12 alkyl group;
a is a nitrogen-containing heterocycle, B is an aromatic ring or a heterocycle;
ring structure a and at least one ring structure B are fused to adjacent ring structures at any position.
In some embodiments of the invention, the fused structure of ring a and ring B is selected from the group consisting of:
11. in some embodiments of the present invention, red-emitting metal complexes are provided having a structure selected from one of:
wherein:
"alkyl" means a saturated aliphatic radical of 1 to 20 carbon atoms, including straight and branched chain radicals (a numerical range referred to herein, e.g., "1 to 20", means that the radical, in this case alkyl, may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms). Preferably, the alkyl group is a medium size alkyl group having 1 to 10 carbon atoms, and more preferably, the alkyl group is an alkyl group having 1 to 8 carbon atoms, such as methyl, ethyl, propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, pentyl, etc.
An "aromatic ring" means an all-carbon monocyclic or fused polycyclic group of 6 to 12 carbon atoms having a completely conjugated pi-electron system. Non-limiting examples of aryl groups are phenyl, naphthyl and anthracenyl.
"heterocycle" means a monocyclic or fused ring group of 5 to 12 ring atoms containing one, two, three or four ring heteroatoms selected from N, O or S, the remaining ring atoms being C, and additionally having or not having a completely conjugated pi-electron system.
General synthetic route:
the specific embodiment of the present invention also provides a preparation method of the above red light metal complex, which is synthesized by the following general synthetic route: mixing an iridium dimeric bridged complex containing two main ligands, a tetraphenylphosphonimide auxiliary ligand and sodium carbonate, wherein the main ligand is any one of phenylisoquinoline, phenylbenzopyridazine, phenylbenzopyrimidine, phenylpyridopyridine and phenylpyridopyrimidine; adding a 2-ethoxyethanol solution, carrying out heating reaction at 120-140 ℃, reacting for 12-48 h, cooling to room temperature, carrying out reduced pressure distillation to remove the solvent, extracting with dichloromethane, concentrating, carrying out column chromatography separation to obtain a crude product of the complex, and sublimating to obtain the pure iridium complex.
Synthesis example:
synthesis of Compound Ir-1
1-chloroisoquinoline (26.39mmol), 2-methylphenylboronic acid (31.66mmol), tetratriphenylphosphine palladium (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-1-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-1-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol), and reacted at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, and the organic layer is concentrated and subjected to column chromatography to obtain the compound Ir-1, wherein the yield is 45.4%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1653.7[ M + ]. Example Synthesis of Ir-2
1-chloroisoquinoline (26.39mmol), 3-methylphenylboronic acid (31.66mmol), tetratriphenylphosphine palladium (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-2-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-2-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, the organic layer is concentrated and subjected to column chromatography to obtain a compound Ir-2, and the yield is 48.2%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1653.7[ M + ].
Example Synthesis of Ir-3
1-chloroisoquinoline (26.39mmol), 4-methylphenylboronic acid (31.66mmol), tetratriphenylphosphine palladium (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-3-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-3-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, and the organic layer is concentrated and subjected to column chromatography to obtain a compound Ir-3, wherein the yield is 57.3%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1653.7[ M + ].
Example Synthesis of Ir-6
1-chloroisoquinoline (26.39mmol), 2, 4-dimethylbenzeneboronic acid (31.66mmol), tetratriphenylphosphorodiamidite (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-6-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-6-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, and the organic layer is concentrated and subjected to column chromatography to obtain a compound Ir-6, wherein the yield is 39.5%. MS (ESI-TOF) Mass-to-Nuclear ratio M/z found 1681.8[ M + ]
Synthesis of Compound Ir-7
1-chloroisoquinoline (26.39mmol), 2, 5-dimethylbenzeneboronic acid (31.66mmol), tetratriphenylphosphorodiamidite (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-7-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-7-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, and the organic layer is concentrated and subjected to column chromatography to obtain a compound Ir-7, wherein the yield is 38.4%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1681.8[ M + ].
Synthesis of Compound Ir-8
1-chloroisoquinoline (26.39mmol), 3, 4-dimethylbenzeneboronic acid (31.66mmol), tetratriphenylphosphorodiamidite (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-8-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-8-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, and the organic layer is concentrated and subjected to column chromatography to obtain a compound Ir-8, wherein the yield is 42.9%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1681.8[ M + ].
Synthesis of Compound Ir-9
1-chloroisoquinoline (26.39mmol), 3, 5-dimethylbenzeneboronic acid (31.66mmol), tetratriphenylphosphorodiamidite (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, added with water and dichloromethane, and the organic layer was concentrated by column chromatography to give the main ligand (Ir-9-L). Dissolving the main ligand (13.08mmol) and iridium trichloride (6.23mmol) in 15mL of 2-ethoxyethanol, reacting the mixture at 130 ℃ for 12h, cooling, adding water, and filtering to obtain a chlorine bridge intermediate (Ir-9-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system is cooled, water and dichloromethane are added, and the organic layer is concentrated and subjected to column chromatography to obtain a compound Ir-9, wherein the yield is 45.7%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1681.8[ M + ].
Synthesis of comparative example CC-1
1-chloroisoquinoline (26.39mmol), phenylboronic acid (31.66mmol), tetrakistriphenylphosphine palladium (0.79mmol) and sodium carbonate (60.00mmol) were dissolved in 100mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, water and dichloromethane were added, and the organic layer was concentrated by column chromatography to give the main ligand (CC-1-L). The main ligand (13.08mmol) and iridium trichloride (6.23mmol) were dissolved in 15mL of 2-ethoxyethanol, the mixture was reacted at 130 ℃ for 12h, cooled, added with water, and filtered to give the chloro-bridged intermediate (CC-1-Cl). The obtained chloro-bridged intermediate was added to 15mL of 2-ethoxyethanol without column chromatography, followed by addition of the ancillary ligand Ktpip (12.46mmol) and reaction at 130 ℃ for 12 hours. The system was cooled, water and dichloromethane were added, the organic layer was concentrated and column chromatographed to give the compound CC-1 in 48.0% yield. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1625.7[ M + ].
Device embodiments
In order to schematically illustrate the excellent characteristics of the material of the present invention, there is also provided an organic electroluminescent device, the structure of the OLED device comprising: the organic light emitting diode comprises a substrate, an anode, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode.
In the device manufacturing process, the substrate is glass, and the anode material is indium tin oxide; the hole transport layer uses N, N, N ', N' -tetra (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine, the electron transport layer uses 3,3'- (5' - (3- (pyridine-3-yl) phenyl) - [1,1':3',1 '-triphenyl ] -3, 3' -diyl) bipyridine, the thickness is 60nm, the evaporation rate is 0.05 nm/s; LiF/Al is adopted as the cathode. The organic light-emitting layer adopts a light-emitting layer with a doped structure, and comprises a main material and a light-emitting material, wherein the main material is 2,2 '-bis (trifluoromethyl) -4,4' -bis (9-carbazole) biphenyl, and the selected light-emitting material is the iridium complex, and the mass fraction of the iridium complex is 5 wt%.
The external quantum efficiency of the device using compound CC-1 is defined as 100. The relevant data are detailed in table 1.
TABLE 1 device Performance data
| Sublimation yield | Quantum efficiency | |
| Ir-1 | 52.7％ | 105 |
| Ir-2 | 51.6％ | 106 |
| Ir-3 | 53.5％ | 108 |
| Ir-6 | 54.1％ | 112 |
| Ir-7 | 52.6％ | 115 |
| Ir-8 | 57.1％ | 116 |
| Ir-9 | 52.5％ | 114 |
| CC-1 | 35.7％ | 100 |
It can be seen that the compounds of the present invention have significantly improved quantum efficiency, synthesis yield and sublimation yield, especially sublimation yield, relative to the comparative compounds.
It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples for carrying out the invention, and that various changes in form and details may be made therein without departing from the spirit and scope of the invention in practice.
Claims (9)
1. A red-emitting metal complex having a structure represented by general formula (I):
wherein,
R1、R2、R3and R4Each independently is a substituted or unsubstituted C1-C12 alkyl group;
m is a metal atom selected from the group consisting of a group VIII metal element, a group IB metal element, a group IA metal element, and a group IIA metal element;
a is a nitrogen-containing heterocycle, B is an aromatic ring or a heterocycle, and ring structure A and at least one ring structure B are fused with adjacent ring structures at arbitrary positions;
m is 2 or 3, n is 1 or 0;
l is an auxiliary ligand.
2. The red-emitting metal complex according to claim 1, wherein L is a bidentate ligand.
3. The red-emitting metal complex according to claim 2, wherein L is a Tpip ligand shown below, and M is Ir, M is 2:
4. the red-emitting metal complex according to claim 3, having a structure represented by general formula (II):
wherein,
R1、R2、R3and R4Each independently is a substituted or unsubstituted C1-C12 alkyl group;
a is a nitrogen-containing heterocycle, B is an aromatic ring or a heterocycle;
ring structure a and at least one ring structure B are fused to adjacent ring structures at any position.
5. The red-emitting metal complex according to claim 1, wherein the fused structure of ring a and ring B is selected from the group consisting of:
6. the red-emitting metal complex according to claim 1, having a structure selected from one of:
7. the method for producing a red-light metal complex according to any one of claims 1 to 6, characterized by comprising the steps of: mixing an iridium dimeric bridged complex containing two main ligands, a tetraphenylphosphonimide auxiliary ligand and sodium carbonate, adding a 2-ethoxyethanol solution, carrying out heating reaction at 120-140 ℃ for 12-48 h, cooling to room temperature, carrying out reduced pressure distillation to remove the solvent, extracting with dichloromethane, concentrating, carrying out column chromatography separation to obtain a crude product of the complex, and sublimating to obtain a pure iridium complex.
8. The method for preparing a red-light metal complex according to claim 7, wherein the primary ligand is any one of phenylisoquinoline, phenylbenzopyridazine, phenylbenzopyrimidine, phenylpyridopyridine, and phenylpyridopyrimidine.
9. Use of the red-emitting metal complex of any one of claims 1 to 6 in an organic electroluminescent material.
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