CN110760305A - Phosphorescent compound, preparation method thereof and organic electroluminescent device comprising phosphorescent compound - Google Patents
Phosphorescent compound, preparation method thereof and organic electroluminescent device comprising phosphorescent compound Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims description 23
- 239000000126 substance Substances 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 13
- 239000010410 layer Substances 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- -1 cyano, carboxyl Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 9
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 4
- 125000000707 boryl group Chemical group B* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 19
- 239000003446 ligand Substances 0.000 abstract description 12
- 230000000052 comparative effect Effects 0.000 abstract description 7
- 150000002736 metal compounds Chemical class 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000543 intermediate Substances 0.000 description 24
- 238000005406 washing Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- 238000012544 monitoring process Methods 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 12
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- 239000000203 mixture Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000000967 suction filtration Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
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- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- 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 3
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 3
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- 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
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
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- 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)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a phosphorescent compound and an organic electroluminescent device comprising the same, and relates to the field of organic electroluminescent materials. The structural formula of the phosphorescent compound is shown in chemical formula 1:
Description
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to a phosphorescent compound, a preparation method thereof and an organic electroluminescent device containing the phosphorescent compound.
Background
The OLED is a hole and electron dual injection type light emitting device, and directly converts electric energy into light energy of organic semiconductor material molecules. Compared with traditional display devices such as a CRT (cathode ray tube), an LCD (liquid crystal display), a PDP (plasma display panel) and the like, the OLED has all the advantages of the existing display, has unique advantages, not only has high brightness, high contrast, high definition, wide visual angle, wide color gamut and the like to realize high-quality images, but also has the characteristics of ultra-thinness, ultra-lightness, low driving voltage, low power consumption, wide temperature and the like to meet the requirements of portable equipment on portability, power saving and outdoor operation; the OLED display has the unique characteristics of self-luminescence, high luminous efficiency, short response time, transparency, flexibility and the like.
The noble metal complex is used as a phosphorescent material, fully utilizes singlet excitons and triplet excitons, only utilizes the singlet excitons compared with a fluorescent material, and effectively utilizes the triplet excitons with the proportion up to 75 percent, so that the PhOLED based on the phosphorescent material realizes 100 percent of internal quantum efficiency. In recent three years, phosphorescent materials gradually replace traditional fluorescent materials, and become hot spots for research on OLED luminescent materials. However, since the synthesis process of the phosphorescent material is complicated, takes a long time, and has a short lifetime, further development of the phosphorescent material is urgently needed.
Disclosure of Invention
In view of the above-mentioned disadvantages of the prior art, the present invention provides a phosphorescent compound, a method of preparing the same, and an organic electroluminescent device comprising the same. The novel phosphorescent compound provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved, and the service life is long.
In order to solve the technical problems, the technical scheme of the invention is as follows:
the invention provides a phosphorescent compound, which has a structural formula shown in chemical formula 1:
in the formula, wherein R1～R4Independently represent: hydrogen, isotopes of hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid, phosphoric acid, boryl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryloxy, or substituted or unsubstituted C6-C60 arylthio;
or R1～R4Are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
n is an integer of 0 to 3;
R1～R4the position of the substituent is any position of the ring; r1～R4The number of (a) is 0-4.
In the above technical scheme, R is preferably selected as1～R4When linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring, the carbon atom is replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur.
In the above technical solution, n is preferably 2; r4Preferably a phosphorus oxy group, or an arylamine group.
In the above technical solution, chemical formula 1 is particularly preferably any one selected from chemical formula 1-1 to chemical formula 1-7:
wherein R is1～R3N is as defined above;
R5、R6、R9、R10each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heterocyclic group, a substituted or unsubstituted C1-C60 alkylamino group, or a substituted or unsubstituted C6-C60 arylamino group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
R7、R8each independently represents hydrogen, an isotope of hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid, phosphoric acid, boryl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryloxy, or substituted or unsubstituted C6-C60 arylthio; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically, aliphatic or aromatic ring of C3-C30.
In the above technical scheme, R5、R6、R9、R10When linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring, respectively, the carbon atom is replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur; r7、R8When linked to adjacent substituents to form a substituted or unsubstituted mono-or polycyclic ring, respectively, the carbon atoms are replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur.
In the above technical solution, it is most preferable that the phosphorescent compound is selected from any one of the following structures:
the invention also provides a preparation method of the phosphorescent compound, which comprises the following steps:
step 1, preparation of intermediate I
Dissolving compound 1 and compound 2 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate I;
step 2, preparation of intermediate II
Dissolving compound 3 and compound 4 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate II;
step 3, preparation of intermediate IV
Reacting intermediate II with IrCl3·3H2Dissolving O into the mixed solution of ethylene glycol ethyl ether/water, and preparing an intermediate III after the reaction is finished; dissolving the intermediate III in dichloromethane, adding an isopropanol solution of silver trifluoromethanesulfonate, and preparing an intermediate IV after the reaction is finished;
step 4, preparation of compound shown in chemical formula 1
Adding ethylene glycol ethyl ether into the intermediate IV and the intermediate I, and preparing a compound shown in a chemical formula 1 after the reaction is finished;
wherein, the definitions of the substituents and the number thereof, and the range definition of n are the same as those in chemical formula 1, and are not repeated herein.
In the above preparation method, the preferred solvent for the synthesis of intermediates I and II is a mixed solvent of toluene, ethanol and water in a molar ratio of 1: 2-3: 2-3, the reaction temperature is not more than 100 ℃, and the reaction time is not more than 24 hours. IrCl3·3H2O and intermediate II in a molar ratio of 1: 2-4 are mixed in a solvent and the mixture is heated under reflux prior to isolation of the diiridium dimer. In the preparation of the compound of formula 1, preferred solvents are ethers or ether/water mixed solvents, such as ethylene glycol ethyl ether and ethylene glycol ethyl ether/water mixtures. The molar ratio of primary ligand to secondary ligand in the final product is determined based on the approximate molar ratio of the reactants (based on composition).
The present invention also provides an organic electroluminescent device prepared from the phosphorescent compound represented by chemical formula 1 of the present invention.
The organic electroluminescent device comprises: the organic light emitting diode comprises a first electrode, a second electrode and an organic layer arranged between the two electrodes, wherein the organic layer contains a phosphorescent compound shown in chemical formula 1.
The organic electroluminescent device comprises a light-emitting layer, wherein the light-emitting layer contains the organic phosphorus luminescent material shown in the chemical formula 1.
The light emitting layer of the organic electroluminescent device includes a host material and a dopant material, and the dopant material contains the organic phosphorus light emitting material represented by chemical formula 1 of the present invention.
The invention has the beneficial effects that:
the phosphorescent compound provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved, and the service life is long.
The preparation method of the phosphorescent compound provided by the invention has the advantages of easily available raw materials, simple synthesis process and higher product yield.
The phosphorescent compounds of the present invention can be applied to OLED light emitting devices and, compared to comparative examples, have improved voltage, efficiency and lifetime over known OLED materials.
Detailed Description
The following are examples of the present invention, which are provided to aid understanding of the present invention and are not intended to limit the scope of the present invention. In addition, the preparation methods of the compounds which are not specifically listed in the embodiments of the present invention are methods generally applied in the related industries, and the methods described in the embodiments can be referred to when preparing other compounds.
Example 1: preparation of Compound 1
① A-001(30mmol, 10.6g), IrC1 was weighed in a nitrogen protection system3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL of ethanol, then washing with 100mL of petroleum ether, and drying to obtain product B-001(10.0g, yield 80%).
② intermediate B-001(4.8mmol, 9.0g) was weighed, silver trifluoromethanesulfonate (14.4mmol, 4.0g) was added, 100mL of dichloromethane was added, 40mL of isopropanol was added, the reaction was carried out at room temperature under nitrogen for 24 hours, monitored by TLC, the reaction was essentially complete, the solution was filtered off with suction to give a dark oil C-001(10.6g, 88% yield).
③ intermediate C-001(10.4mmol, 10.0g) is weighed, ligand D-001(32.3mmol, 10.9g) is added, 150mL of absolute ethyl alcohol is added into the system, the mixture is stirred and reacted for 24 hours at 90 ℃ under the protection of nitrogen, a large amount of solid is separated out, TLC monitoring is carried out, the raw material basically reacts, suction filtration is carried out, crude product of target product is obtained, about 50mL of petroleum ether is used for washing, and drying is carried out, thus obtaining compound 1(9.5g, 73% of yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1252.43; the test value was 1253.41.
Example 2: preparation of Compound 7
① A-007(30mmol, 12.2g), IrC1 was weighed out under nitrogen protection3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL of ethanol, then washing with 100mL of petroleum ether, and drying to obtain the product B-007(10.3g, yield 80%).
② intermediate B-007(4.8mmol, 9.9g) was weighed out, silver trifluoromethanesulfonate (14.4mmol, 4.0g) was added, 100mL of dichloromethane and 40mL of isopropanol were added to the system, and the mixture was reacted at room temperature for 24 hours under nitrogen protection, monitored by TLC, after the starting material had reacted substantially, the solution was filtered off with suction to obtain a dark colored oil C-007(11.5g, 86% yield).
③ intermediate C-007(10.77mmol, 11.5g) is weighed, ligand D-007(32.3mmol, 10.4g) is added, 150mL of absolute ethyl alcohol is added into the system, the mixture is stirred and reacted for 24 hours at 90 ℃ under the protection of nitrogen, a large amount of solid is separated out, TLC monitoring is carried out, the raw materials are basically reacted, suction filtration is carried out, crude products of target products are obtained, and the crude products are washed by about 50mL of petroleum ether and dried to obtain compound 7(10.8g, 76% of yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1319.84; the test value was 1319.83.
Example 3: preparation of Compound 11
① A-011(30mmol, 10.67g), IrC1 were weighed out under nitrogen protection3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 80mL of ethanol, then washing with 120mL of petroleum ether, and drying to obtain the product B-011(9.45g, 80% yield).
② intermediate B-011(4.7mmol, 9.0g) was weighed out, silver trifluoromethanesulfonate (14.4mmol, 4.0g) was added, 100mL of dichloromethane was added to the system, 40mL of isopropanol was added, the reaction was carried out at room temperature under nitrogen protection for 24 hours, monitored by TLC, the reaction was essentially complete, a dark solution was filtered off with suction, and the product was spin-dried to give C-011(9.4g, 81% yield) as a dark oil.
③ intermediate C-011(10.5mmol, 9.4g) is weighed, ligand A-011(32.3mmol, 5.8g) is added, 150mL of absolute ethyl alcohol is added into the system, the mixture is stirred and reacted for 24 hours at 90 ℃ under the protection of nitrogen, a large amount of solid is separated out, TLC monitoring is carried out, the raw material basically reacts, suction filtration is carried out, crude products of target products are obtained, the crude products are washed by about 50mL of petroleum ether, and the compound 11(9.0g, 80% of yield) is obtained after drying.
HPLC purity is more than 99%.
Mass spectrum calculated 1255.3; the test value was 1255.2.
Example 4: preparation of Compound 19
① A-019(30mmol, 10.7g), IrC 1g were weighed in a nitrogen protected system3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL of ethanol, then washing with 100mL of petroleum ether, and drying to obtain product B-019(11.9g, yield 86%).
② intermediate B-019(4.8mmol, 10.0g) was weighed, silver trifluoromethanesulfonate (14.4mmol, 4.0g) was added, 100mL of dichloromethane and 40mL of isopropanol were added to the system, the reaction was carried out at room temperature under nitrogen protection for 24 hours, monitored by TLC, after the starting material had reacted substantially, a dark solution was obtained by suction filtration and dried to give C-019(10.4g, 87% yield) as a dark oil.
③ intermediate C-019(10.77mmol, 10.4g) is weighed, ligand D-019(32.3mmol, 5.8g) is added, 150mL of absolute ethanol is added into the system, the mixture is stirred and reacted for 24 hours at 90 ℃ under the protection of nitrogen, a large amount of solid is separated out, TLC monitoring is carried out, the raw material basically reacts, suction filtration is carried out, crude product of target product is obtained, about 50mL of petroleum ether is used for washing, and drying is carried out, thus obtaining compound 19(9.7g, yield 83%).
HPLC purity is more than 99%.
Mass spectrum calculated 1082.18; the test value was 1082.19.
Example 5: preparation of Compound 44
① A-044(30mmol, 12.2g), IrC1 was weighed in a nitrogen protection system3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL ethanol, washing with 100mL petroleum ether, and drying to obtain product B-044(11.4g, 82% yield).
② intermediate B-044(4.8mmol, 10.0g) was weighed, silver trifluoromethanesulfonate (14.4mmol, 4.0g) was added, 100mL of dichloromethane was added, 40mL of isopropanol was added, the reaction was carried out at room temperature under nitrogen for 24 hours, monitored by TLC, the starting material was essentially reacted, filtered off with suction to obtain a dark solution, and dried by spinning to obtain C-044 as a dark oil (11.5g, 86% yield).
③ intermediate C-044(11.5mmol, 12.6g) is weighed, ligand D-044(32.3mmol, 8.8g) is added, 150mL of absolute ethyl alcohol is added into the system, the mixture is stirred and reacted for 24 hours at 90 ℃ under the protection of nitrogen, a large amount of solid is separated out, TLC monitoring is carried out, the raw material basically reacts, suction filtration is carried out, crude product of target product is obtained, about 50mL of petroleum ether is used for washing, and drying is carried out, thus obtaining compound 44(12.1g, yield 83%).
HPLC purity is more than 99%.
Mass spectrum calculated 1271.43; the test value was 1271.41.
Example 6: preparation of Compound 55
① A-055(30mmol, 11.2g), IrC 1g were weighed out under nitrogen protection3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL of ethanol, then washing with 100mL of petroleum ether, and drying to obtain the product B-055(9.8g, 82% yield).
② intermediate B-055(4.8mmol, 9.3g) was weighed out, silver trifluoromethanesulfonate (14.4mmol, 4.0g) was added, 100mL dichloromethane was added, 40mL isopropanol was added, the reaction was carried out at room temperature under nitrogen for 24 h, monitored by TLC, the starting material was essentially reacted and filtered off with suction to obtain a dark solution, which was spun dried to obtain C-055 as a dark oil (9.4g, 86% yield).
③ intermediate C-055(10.77mmol, 9.4g) was weighed, ligand D-055(32.3mmol, 8.0g) was added, 150mL of absolute ethanol was added to the system, the reaction was stirred at 90 deg.C for 24 hours under nitrogen protection, a large amount of solid precipitated, TLC monitored, the starting material reacted essentially, suction filtered to obtain the crude product, washed with about 50mL of petroleum ether, and dried to obtain compound 55(10.0g, 73% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1179.45; the test value was 1179.46.
Example 7: preparation of Compound 58
① A-058(30mmol, 10.7g), IrC1 was weighed out under nitrogen protection3·3H2O (12.5mmol, 4.4g) is put into the reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, the temperature is raised to 140 ℃ under the protection of nitrogen, and the reaction is stirred for 24 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL of ethanol, then washing with 100mL of petroleum ether, and drying to obtain the product B-058(9.0g, yield 80%).
② intermediate B-058(4.8mmol, 9.0g) is weighed, silver trifluoromethanesulfonate (14.4mmol, 4.0g) is added, 100mL of dichloromethane and 40mL of isopropanol are added to the system, the reaction is carried out at room temperature for 24 hours under the protection of nitrogen, TLC monitoring is carried out, the raw materials are basically reacted completely, a dark solution is obtained by suction filtration, and the dark oily substance C-058(10.8g, 86% yield) is obtained by spin drying.
③ intermediate C-058(10.77mmol, 10.8g) is weighed, ligand D-058(32.3mmol, 10.4g) is added, 150mL of absolute ethyl alcohol is added into the system, the mixture is stirred and reacted for 24 hours at 90 ℃ under the protection of nitrogen, a large amount of solid is separated out, TLC monitoring is carried out, the raw material basically reacts, suction filtration is carried out, crude product of target product is obtained, and the crude product is washed by about 50mL of petroleum ether and dried, thus obtaining compound 58(9.0g, yield 70%).
HPLC purity is more than 99%.
Mass spectrum calculated 1136.36; the test value was 1136.35.
The present invention also provides an organic electroluminescent device made of the phosphorescent compound represented by chemical formula 1 of the present invention.
In order to further describe the present invention, more specific examples are set forth below.
Example 8
An organic electroluminescent device was prepared using the phosphorescent compound of compound 1, which is more specifically:
coating with a thickness of
The ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. Firstly, evaporating N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine ('2-TNATA') 60nm on an ITO (anode), and then evaporating NPB 60nm, a main substance 4,4'-N, N' -biphenyl dicarbazole ('CBP') and a doping substance compound 195: 5 in a weight ratio to mix and evaporate 30nm, evaporate a hole blocking layer ('BALq') 10nm, evaporate an electron transport layer 'Alq 3' 40nm, evaporate an electron injection layer LiF0.2nm and evaporate cathode Al 150nm to prepare the organic electroluminescent device. And testing the performance luminescence characteristics of the obtained device, wherein a KEITHLEY2400 type source measuring unit and a CS-2000 spectral radiance luminance meter are adopted for measurement so as to evaluate the driving voltage, the luminescence brightness and the luminescence efficiency.
Example 9
An organic electroluminescent device was produced as in example 8, except that the compound doping the light-emitting layer was replaced with compound 7 from compound 1.
Example 10
An organic electroluminescent device was produced as in example 8, except that the compound doping the light-emitting layer was replaced with compound 11 from compound 1.
Example 11
An organic electroluminescent device was produced as in example 8, except that the compound doping the light-emitting layer was replaced with compound 19 from compound 1.
Example 12
An organic electroluminescent device was produced as in example 8, except that the compound for doping the light-emitting layer was replaced with compound 44 from compound 1.
Example 13
An organic electroluminescent device was produced as in example 8, except that the compound doping the light-emitting layer was replaced with compound 55 from compound 1.
Example 14
An organic electroluminescent device was produced as in example 8, except that the compound for doping the light-emitting layer was replaced from compound 1 to compound 58.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 8, except that the dopant compound was replaced from compound 1 to the following compound:
table 1 results of testing organic electroluminescent elements in examples 8 to 14 and comparative example 1
| Compound (I) | Drive voltage (V) | Efficiency of | Life (h) | Colour(s) |
| Ir(ppy)3 | 1.0 | 1.0 | 1.0 | Green |
| 1 | 0.56 | 3.8 | 5.8 | Green |
| 7 | 0.53 | 3.5 | 5.2 | Green |
| 11 | 0.55 | 3.8 | 5.0 | Green |
| 19 | 0.56 | 3.6 | 5.1 | Green |
| 44 | 0.51 | 3.5 | 5.0 | Green |
| 55 | 0.50 | 3.7 | 5.1 | Green |
| 58 | 0.55 | 3.3 | 4.9 | Green |
The device test performance was measured by referring to comparative device 1, and each performance index of comparative device 1 was set to 1.0. From the results of table 1, it can be seen that the compounds of the present invention can be applied to OLED light emitting devices, and compared to comparative examples, the voltage, efficiency and lifetime are improved compared to known OLED materials.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A phosphorescent compound having a structural formula shown in chemical formula 1:
in the formula, wherein R1～R4Independently represent: hydrogen, isotopes of hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic, phosphonic, boryl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkaneA group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylamino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C6-C60 aryloxy group, or a substituted or unsubstituted C6-C60 arylthio group;
or R1～R4Are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
n is an integer of 0 to 3;
R1～R4the position of the substituent is any position of the ring; r1～R4The number of (a) is 0-4.
2. The phosphorescent compound according to claim 1, wherein when R is1～R4When linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring, the carbon atom is replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur.
3. The phosphorescent compound according to claim 1, wherein n is 2; r4Is a phosphorus oxy group or an arylamine group.
4. The phosphorescent compound according to claim 1, wherein chemical formula 1 is specifically selected from any one of chemical formulae 1-1 to 1-7:
wherein R is1～R3N is as defined above;
R5、R6、R9、R10each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heterocyclic group, a substituted or unsubstituted C1-C60 alkylamino group, or a substituted or unsubstituted C6-C60 arylamino group; or linked to an adjacent substituent to form a substituted or unsubstitutedSubstituted mono-or polycyclic, in particular aliphatic or aromatic rings from C3 to C30;
R7、R8each independently represents hydrogen, an isotope of hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid, phosphoric acid, boryl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryloxy, or substituted or unsubstituted C6-C60 arylthio; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically, aliphatic or aromatic ring of C3-C30.
5. The phosphorescent compound of claim 4, wherein R is5、R6、R9、R10When linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring, respectively, the carbon atom is replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur; r7、R8When linked to adjacent substituents to form a substituted or unsubstituted mono-or polycyclic ring, respectively, the carbon atoms are replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur.
6. Phosphorescent compound according to claim 1, characterized in that it is selected from any of the following structures:
7. a method for preparing a phosphorescent compound according to any one of claims 1 to 6, comprising the steps of:
step 1, preparation of intermediate I
Dissolving compound 1 and compound 2 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate I;
step 2, preparation of intermediate II
Dissolving compound 3 and compound 4 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate II;
step 3, preparation of intermediate IV
Reacting intermediate II with IrCl3·3H2Dissolving O into the mixed solution of ethylene glycol ethyl ether/water, and preparing an intermediate III after the reaction is finished; dissolving the intermediate III in dichloromethane, adding an isopropanol solution of silver trifluoromethanesulfonate, and preparing an intermediate IV after the reaction is finished;
step 4, preparation of compound shown in chemical formula 1
Adding ethylene glycol ethyl ether into the intermediate IV and the intermediate I, and preparing a compound shown in a chemical formula 1 after the reaction is finished;
8. an organic electroluminescent device prepared from the phosphorescent compound of any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, comprising: a first electrode, a second electrode and an organic layer interposed between the two electrodes, wherein the organic layer contains the phosphorescent compound according to any one of claims 1 to 6.
10. The organic electroluminescent device according to claim 9, comprising a light-emitting layer containing the phosphorescent compound according to any one of claims 1 to 6.
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| CN114456462A (en) * | 2021-10-13 | 2022-05-10 | 中国科学院江西稀土研究院 | High-weather-resistance light conversion film and preparation method and application thereof |
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