CN115368393A - 一种基于三芳基硼并嘧啶有机化合物及其应用 - Google Patents
一种基于三芳基硼并嘧啶有机化合物及其应用 Download PDFInfo
- Publication number
- CN115368393A CN115368393A CN202211041445.5A CN202211041445A CN115368393A CN 115368393 A CN115368393 A CN 115368393A CN 202211041445 A CN202211041445 A CN 202211041445A CN 115368393 A CN115368393 A CN 115368393A
- Authority
- CN
- China
- Prior art keywords
- group
- triaryl
- independently represents
- organic compound
- boraopyrimidine
- 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.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 55
- -1 boron pyrimidine organic compounds Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005067 haloformyl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 150000001336 alkenes Chemical group 0.000 claims description 2
- 150000001345 alkine derivatives Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000002096 quantum dot Substances 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- VINBVOMNIBDIPH-UHFFFAOYSA-N isocyanoimino(oxo)methane Chemical compound O=C=N[N+]#[C-] VINBVOMNIBDIPH-UHFFFAOYSA-N 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052796 boron Inorganic materials 0.000 abstract description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- SAZXDUHRKOQVCZ-UHFFFAOYSA-N N1=CN=CC=C1.[B] Chemical compound N1=CN=CC=C1.[B] SAZXDUHRKOQVCZ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- ZTYYDUBWJTUMHW-UHFFFAOYSA-N furo[3,2-b]furan Chemical compound O1C=CC2=C1C=CO2 ZTYYDUBWJTUMHW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004807 phenyl sulfones Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical compound C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- 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
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/10—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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
-
- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1085—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with other heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明公开了一种基于三芳基硼并嘧啶有机化合物及其应用,属于有机光电材料技术领域。本发明构建了一系列具有高效的TADF性能的三芳基硼并嘧啶有机化合物,获得的了具有窄半峰宽的TADF分子,解决了目前MR‑TADF分子发光区域大都集中在蓝绿光的现状。本发明将三芳基硼杂螺烯骨架引入了喹唑啉分子,构建了具有窄半峰宽的TADF分子,获得了了高效率、高色纯度的有机电致发光材料,并且喹唑啉基团的存在使得材料发光波长发生较为明显的红移成功构建了一系列具有高效的TADF性能的有机发光材料。
Description
技术领域
本发明涉及一种基于三芳基硼并嘧啶有机化合物及其应用,属于有机光电材料技术领域,尤其涉及三芳基硼并嘧啶有机化合物、聚合物、混合物、组合物及其用途。
背景技术
有机发光材料合成容易、易于衍生及光电特性优异等特点使得有机发光二极管(OLED)在照明及显示等领域具有很大的应用价值及商业化潜力。目前为止,基于荧光及磷光的发光材料体系已经被开发出来。基于荧光材料的有机发光二极管具有较高的稳定性,这是因为在电激发下其内量子效率仅为25%,仅有单线态激子被利用,较低的内量子效率使得器件性能受限。基于磷光材料的有机发光二极管则可以实现几乎100%的激子利用率,然而目前高效的磷光材料均离不开价格昂贵的过渡金属(如铂、铱、铑等)。
近年来发展的热激活延时荧光(TADF)材料也可以实现100%的激子利用率,与磷光材料相比,TADF材料不含贵金属的特性可以降低其成本。目前报道的实现TADF机制提高器件性能的方式包括利用TADF发光客体和利用激基复合物两种方式。
在高效TADF材料的发展过程中,纯有机TADF材料具有巨大的发展前景,已在短短的几年里取得了巨大的进步。为了设计高效的纯有机TADF材料,研究工作者们致力于缩小分子最低单重态(S1)和三重态(T1)之间的能级差(ΔES-T)、增强分子的辐射跃迁速率、抑制分子的非辐射跃迁。这些研究主要集中在以下五个方面:第一,合成并优化给体种类,如:都包含了二苯胺单元的吩嗪、吩噻嗪、吩恶嗪、咔唑、吖啶等;第二,采用合适的受体,目前常见的受体包括芳腈、三嗪、苯砜以及其衍生物;第三:改变给体或者受体基团的强弱,包括给/受体环内杂原子个数及其周围基团种类和数量;第四,调整分子的取向、对称性及刚性等;第五,选择适当的连接方式,如增加给体和受体之间的距离、分子连接的位置。通过使用这些方法,TADF OLEDs的量子效率得到了很大的提高。例如,日本九州大学Adachi课题组报道了效率高达19.5%纯蓝色TADF OLEDs,韩国首尔大学J.-J.Kim课题组实现了最大量子效率为29.6%绿光TADF器件,发光效率已经达到了磷光OLEDs水平。
目前大部分的TADF发光材料由电子给体(donor,D)和电子受体(acceptor,A)构成。最高占据轨道(HOMO)和最低未占据空轨道(LUMO)电子云的重叠程度较小,单三线态能级差较小。并且由于大部分TADF发光材料的光谱会因较为扭曲的结构导致半峰宽较宽,且存在效率滚降(roll-off)较大的问题。
目前基于氮硼的刚性杂环的多重共振TADF材料(MR-TADF)与传统TADF材料不同的是,该发光材料具有刚性的平面骨架,利用氮原子(N)和硼原子(B)的相反的共振效应而实现材料的HOMO/LUMO分离,继而基于N/B体系的其他MR-TADF材料逐渐被报道,研究发现当用氧原子替换氮原子作为供电子基团时,形成的多环骨架并没有TADF现象,这说明在高性能MR-TADF材料的设计上虽然取得了巨大的进步,但目前已发现的TADF材料较少,在遵循大框架设计理论的基础之上,获得高性能MR-TADF材料的根本途径是开发新体系,主要是包括开发新的受体和给体材料。此外,相比于给体材料,可选择的受体材料极其紧缺,迫切需要开发新的受体材料,来构筑具有高性能的TADF材料。
发明内容
本发明构建了一系列具有高效的TADF性能的三芳基硼并嘧啶有机化合物,获得的了具有窄半峰宽的TADF分子,解决了目前MR-TADF分子发光区域大都集中在蓝绿光的现状。
本发明的技术方案:
本发明的目的之一是提供一种基于三芳基硼并嘧啶有机化合物,该化合物的通式结构为:
式中,Ar1~Ar6各自独立地代表C2~C20的芳香族、杂芳香族或非芳香族环系;Ar1~Ar6的环上具有相同或不同基团R5,R1-R5各自独立地具有一个含有供电子基团和/或有一个含有吸电子基团;Y1-Y6各自独立地代表单键、二桥基或三桥基。
进一步限定,Ar1~Ar6各自独立地代表以下任一基团:
其中,X在同一基团有多个时,每个X各自独立地代表N或CR3;Z在同一基团有多个时,每个Z各自独立地代表CR4R5、SiR4R5、NR6、C(=O)、S(=O)、S(=O)2、S或O。
进一步限定,Y1-Y6各自独立地代表单键或如下任一二桥基或三桥基:
式中,R7和R8各自独立地代表H、F、Cl、Br、I、D、CN、NO2、CF3、B(OR2)2或Si(R2)3,虚线表示任一二桥基或三桥基与相邻的结构单元键合的键。
进一步限定,R1-R5各自独立地代表具有一个含有供电子基团和/或有一个含有吸电子基团的C1-C20的直链烷烃、C1-C20的烷氧基、C1-C20的硫代烷氧基、C3-C20的支链烷烃、C3-C20的环状烷基、C3-C20的甲硅烷基、C1-C20的酮基、C2-C20的烷氧基羰基、C7-C20的芳香基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、酯基、三氟甲基、H、D、Cl、Br、I、F、可交联的基团、C5-C40的取代或者未取代的芳香族或杂芳族环系、C5-C40的取代或者未取代的芳氧基或杂芳氧基中一种或多种。
进一步限定,该化合物中至少一个R5与其他基团键合的环形成单环或多环的脂肪族或芳族环,或者多个R5之间形成单环或多环的脂肪族或芳族环。
进一步限定,供电子基团为以下任一基团:
进一步限定,吸电子基团为以下任一基团:
式中,n为1、2或3;M1-M8各自独立地代表CR2或N,Y1-Y6中至少有一个是N;Z1-Z3各自独立地代表单键、O、S、CR2;其中R为氢、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基或杂芳基。
进一步限定,该化合物的具体结构式为:
本发明的目的之二是提供一种三芳基硼并嘧啶高聚物,该高聚物的重复单元包含上述的三芳基硼并嘧啶有机化合物的结构。
本发明的目的之三是提供一种三芳基硼并嘧啶混合物,该混合物包含上述三芳基硼并嘧啶有机化合物或上述三芳基硼并嘧啶高聚物,及至少一种有机功能材料。
进一步限定,有机功能材料为空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、发光材料或主体材料。
本发明的目的之四是提供一种三芳基硼并嘧啶组合物,该组合物包含上述三芳基硼并嘧啶有机化合物或上述三芳基硼并嘧啶高聚物,及至少一种有机溶剂。
本发明的目的之四是提供一种有机电子器件,该有机电子器件具有电致发光功能,使用上述三芳基硼并嘧啶有机化合物或上述三芳基硼并嘧啶高聚物作为发光层材料。
本发明的目的之五是提供一种上述三芳基硼并嘧啶有机化合物的应用,该化合物作为发光材料、发光材料、TADF主体材料和量子点主体材料使用。
本发明将三芳基硼杂螺烯骨架引入了喹唑啉分子,构建了具有窄半峰宽的TADF分子,获得了了高效率、高色纯度的有机电致发光材料,并且喹唑啉基团的存在使得材料发光波长发生较为明显的红移,进一步地解决了目前MR-TADF分子发光区域大都集中在蓝绿光的现状。此外,本发明构建了一系列具有高效的TADF性能的有机发光材料,并提供了相应的有效合成路线,获得一类新型高效TADF材料,实现高效率低成本的OLED。
附图说明
图1实施例1获得的产品7的光谱图;
图2实施例2获得的产品5的光谱图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅用以解释本发明,并不用于限定本发明。
下述实施例中所使用的实验方法如无特殊说明均为常规方法。所用材料、试剂、方法和仪器,未经特殊说明,均为本领域常规材料、试剂、方法和仪器,本领域技术人员均可通过商业渠道获得。
具体实施例方式一:
本具体实施方式的三芳基硼并嘧啶有机化合物的结构如下通式(1)或(2)所示:
式中,Ar1~Ar6相同或不同,Ar1~Ar6各自独立地选自2-20个碳原子的芳香族、杂芳香族或非芳香族环系;Ar1~Ar6的环上具有基团R5,R5在每次出现时相同或不同;R1-R5各自独立地具有一个含有供电子基团和/或有一个含有吸电子基团。
具体的R1-R5为H、D、具有1-20个碳原子的直链烷烃、具有1-20个碳原子的烷氧基、具有1-20个碳原子的硫代烷氧基、具有3-20个碳原子的支链、具有3-20个碳原子的环状的烷基、具有3-20个碳原子的甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳香基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、酯基、三氟甲基、Cl、Br、I、F、可交联的基团,含有5-40个环原子的取代或者未取代的芳香族或杂芳族环系,具有含有5-40个环原子的取代或者未取代的芳氧基或杂芳氧基的一种或多种;其中至少一个R5基团与所述基团键合的环形成单环或多环的脂肪族或芳族环,或者多个R5相互之间形成单环或多环的脂肪族或芳族环。
芳香族基团指至少包含一个芳环的烃基。杂环芳香环基团脂指至少包含一个杂原子的芳香烃基。稠环芳香基团指芳香基团的环可以为两个或多个环,其中两个碳原子被相邻的两个环共用。稠杂环芳香基团指至少包含一个杂原子的稠环芳香烃基。对于本发明的目的,芳香基团或杂环芳香基团不仅包括芳香环体系,而且包含非芳香族的环系。因此吡啶、噻吩、吡咯、三唑、咪唑、噁唑、噁二唑、噻唑、四唑、吡嗪、哒嗪、嘧啶、三嗪、卡宾等体系,对于该发明目的同样认为是芳香基团或杂环芳香基团。对于本发明的目的,稠环芳香族或稠杂环芳香族环系不仅包括芳香基团和杂芳香基团的体系,而且其中多个芳香基团或杂环芳香基团也可以被短的非芳香基团间断(小于10%的非H原子,优选小于5%的非H原子,比如C、N或O原子)。因此比如9,9’-螺二芴、9,9’-二芳基芴、三芳胺、二芳基醚、等体系对于该发明目的同样认为是稠环芳香环系。
具体地稠环芳香基团的例子有:萘、蒽、荧蒽、菲、苯并菲、二萘嵌苯,并四苯、并五苯、芘、苯并芘、苊、苯并苊、芴及其衍生物。
具体地稠杂环芳香基团的例子有:苯并呋喃、苯并噻吩、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑林、喹唑啉酮及其衍生物
Y1-Y6相同或者不相同,Y1-Y6各自独立地选自单键、二桥或三桥联基,Y1-Y6各自独立地与其相邻的三个基团以单键或双键相连。
具体实施例方式二:
本具体实施方式与具体实施方式一不同处为:Ar1-Ar6各自独立地包含至少一种如下结构的基团:
其中:Y1-Y6各自独立地表示S、O、NR6、CR7R8、SiR7R8、C(=O)、S(=O)或S(=O)2;R6、R7、R8的定义同R5。
具体实施例方式三:
本具体实施方式与具体实施方式一不同处为:Ar1-Ar6各自独立地为包含至少一种如下结构的基团,其中环上的氢可以被任意取代:
具体实施例方式四:
本具体实施方式与具体实施方式一不同处为:二桥或三桥联基选自以下基团:
其中R3和R4与R5定义相同,虚线表示与相邻基团键合的键。
具体实施例方式五:
本具体实施方式与具体实施方式一不同处为:Y1-Y6不存在,或各自独立地选自以下基团:
其中R基可以成环。
具体实施例方式六:
本具体实施方式与具体实施方式一不同处为:三芳基硼并嘧啶化合物中的NH上的H原子或者桥联基CH2可以被R5基团取代。R5基团可选自具有1-20个碳原子的烷基、具有1-20个碳原子的烷氧基或者具有2-10个碳原子的芳基或杂芳基。其中,具有1-20个碳原子的烷基可以选自甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、2-甲基丁基、正戊基、正己基、环己基、正庚基、环庚基、正辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、戊炔基、己炔基或辛炔基。具有1-10个碳原子的烷氧基可以选自甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基或2-甲基丁氧基。具有2-20个碳原子的芳基或杂芳基取决于用途可以是一价或者二价的,在每一种情况下也可以被上述提及的基团R5取代并可以通过任何希望的位置与芳香族或杂芳香族环连接。进一步,具有2-20个碳原子的芳基或杂芳基可以选自苯、萘、蒽、二萘嵌苯、二氢芘、屈、茈、荧蒽、丁省、戊省、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、硫芴、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、二氮蒽、1,5-二氮杂蒽、氮咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,5-四嗪、1,2,3,4-四嗪、嘌呤、蝶啶、中氮茚或苯并噻二唑。
具体实施例方式七:
本具体实施方式与具体实施方式一不同处为:Ar1-Ar6为苯基。
实施例1:
本实施例合成三芳基硼并嘧啶有机化合物的反应过程如下:
具体合成过程包括以下步骤:
(1)氮气保护、室温搅拌的条件下在250mL的双口烧瓶中加入反应原料1(5g,28.88mmol),尿素(17.35g,288.82mmol),升温度至170℃,反应0.5min产物固化。将反应冷却至100℃,倒入20mL水中稀释并充分搅拌,通过抽滤获得沉淀,用水洗涤并充分干燥,无需进一步纯化,最终得到2.60g白色固体(反应原料2),产率为45.4%。
(2)氮气保护、室温搅拌的条件下在250mL的三口烧瓶中加入反应原料2(2.5g,12.62mmol),苯酚(2.85g,30.28mmol),碳酸钾(6.98g,50.47mmol)和100mLN,N-二甲基甲酰胺,升温度至100℃,回流反应24h。反应结束后,冷却至室温,先通过抽滤除去无机盐,所得滤液通过减压蒸馏除去反应体系中的溶剂,再加入硅胶粉后旋干,用溶剂乙酸乙酯/石油醚(1/1)过柱子后得到3.4g纯产品(中间体3),产率约为77.8%。
(3)将中间体3(3.00g,8.66mmol)悬浮在三氯氧磷(16.42mL,173.24mmol)中,加热回流26h,冷却至室温,减压浓缩,倒入50mL冰水中稀释并充分搅拌,通过抽滤得到沉淀,用水洗涤并充分干燥,无需进一步纯化,最终得到2.20g灰色固体(中间体4),产率约为66.3%。
(4)氮气保护、室温搅拌的条件下在250mL的三口烧瓶中加入中间体4(2g,5.22mmol),苯硼酸(763.60mg,6.26mmol),四三苯基膦钯(603.08mg,521.88μmol),碳酸钾(2.16g,15.66mmol),150mL甲苯和15mL水,升温度至110℃,回流反应24h。反应结束后,冷却至室温,通过减压蒸馏除去反应体系中的大部分溶剂,再加入硅胶粉后旋干,用溶剂二氯甲烷/石油醚(3/2)过柱子后得到1.60g纯产品(中间体5),产率约为72.2%。
(5)氮气保护、室温搅拌的条件下在250mL的三口烧瓶中加入中间体5(1.5g,3.53mmol),4-硼酸苯基咔唑(1.22g,4.24mmol),四三苯基膦钯(407.97mg,353.04μmol),碳酸钾(1.46g,10.59mmol),150mL甲苯和15mL水,升温度至110℃,回流反应24h。反应结束后,冷却至室温,通过减压蒸馏除去反应体系中的大部分溶剂,再加入硅胶粉后旋干,用溶剂二氯甲烷/石油醚(3/2)过柱子后得到1.65g纯产品(中间体6),产率约为74.0%。
(5)氮气保护、冰浴搅拌的条件下在100mL的三口烧瓶中加入中间体6(1.5g,2.37mmol),三溴化硼(1.22g,4.24mmol)和50mL邻二氯苯,升温度至180℃,回流反应24h。冷却至0℃,加入二异丙基乙基胺(547.16mg,4.75mmol),升温度至180℃,回流反应24h。反应结束后,冷却至室温,通过减压蒸馏除去反应体系中的大部分溶剂,再加入硅胶粉后旋干,用溶剂二氯甲烷/石油醚(3/2)过柱子后得到1.02g纯产品(产品7),产率约为67.2%。
实施例2:
本实施例合成三芳基硼并嘧啶有机化合物的反应过程如下:
具体合成过程包括以下步骤:
(1)氮气保护、室温搅拌的条件下在250mL的双口烧瓶中加入反应原料1(5g,16.95mmol),尿素(10.18g,169.53mmol),升温度至170℃,反应0.5min产物固化。将反应冷却至100℃,倒入20mL水中稀释并充分搅拌,通过抽滤获得沉淀,用水洗涤并充分干燥,无需进一步纯化,最终得到3.10g白色固体(中间体2),产率为51.2%。
(2)将中间体2(3.00g,9.38mmol)悬浮在三氯氧磷(17.78mL,187.54mmol)中,加热回流26h,冷却至室温,减压浓缩,倒入50mL冰水中稀释并充分搅拌,通过抽滤得到沉淀,用水洗涤并充分干燥,无需进一步纯化,最终得到2.80g灰色固体(反应原料3),产率约为83.7.3%。
(3)氮气保护、室温搅拌的条件下在250mL的三口烧瓶中加入反应原料3(2.5g,7.01mmol),二苯胺(5.93g,35.03mmol),三二亚苄基丙酮二钯(641.92mg,700.62μmol),三叔丁基膦(141.75mg,700.62μmol),叔丁醇钠(67.33mg,700.62μmol)和100mL甲苯,升温度至110℃,回流反应24h。反应结束后,冷却至室温,先通过硅藻土抽滤除去无机盐,所得滤液通过减压蒸馏除去反应体系中的溶剂,再加入硅胶粉后旋干,用溶剂乙酸乙酯/石油醚(1/1)过柱子后得到4.2g纯产品(中间体4),产率约为75.0%。
(4)氮气保护、冰浴搅拌的条件下在100mL的三口烧瓶中加入中间体4(2.00g,2.50mmol),三溴化硼(1.25g,5.01mmol)和50mL邻二氯苯,升温度至180℃,回流反应24h。冷却至0℃,加入二异丙基乙基胺(64.05mg,5.01mmol),升温度至180℃,回流反应24h。反应结束后,冷却至室温,通过减压蒸馏除去反应体系中的大部分溶剂,再加入硅胶粉后旋干,用溶剂二氯甲烷/石油醚(3/2)过柱子后得到1.30g纯产品(产品5),产率约为64.4%。
对实施例1和实施例2制备得到的最终产物三芳基硼并嘧啶有机化合物的结构进行表征,结果如下:
产品7:MS(EI)m/z:639.196[M+].Calcd for C44H26BN3O2:639.212.Elementalanalysis(calculated,found for C44H26BN3O2):C(82.64%,82.49%),H(4.10%,4.15%),N(6.57%,6.64%)。
产品5:MS(EI)m/z:806.341[M+].Calcd for C56H39BN6:806.333.Elementalanalysis(calculated,found for C56H39BN6):C(83.37%,83.43%),H(4.87%,4.73%),N(10.42%,10.56%)。
对实施例1和实施例2制备得到的最终产物三芳基硼并嘧啶有机化合物的发光性能进行表征,光谱分别如图1和图2所示。
虽然本发明已以较佳的实施例公开如上,但其并非用以限定本发明,任何熟悉此技术的人,在不脱离本发明的精神和范围内,都可以做各种改动和修饰,因此本发明的保护范围应该以权利要求书所界定的为准。
Claims (10)
4.根据权利要求1所述的一种基于三芳基硼并嘧啶有机化合物,其特征在于,R1-R5各自独立地代表具有一个含有供电子基团和/或有一个含有吸电子基团的C1-C20的直链烷烃、C1-C20的烷氧基、C1-C20的硫代烷氧基、C3-C20的支链烷烃、C3-C20的环状烷基、C3-C20的甲硅烷基、C1-C20的酮基、C2-C20的烷氧基羰基、C7-C20的芳香基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、酯基、三氟甲基、H、D、Cl、Br、I、F、可交联的基团、C5-C40的取代或者未取代的芳香族或杂芳族环系、C5-C40的取代或者未取代的芳氧基或杂芳氧基中一种或多种;所述化合物中至少一个R5与其他基团键合的环形成单环或多环的脂肪族或芳族环,或者多个R5之间形成单环或多环的脂肪族或芳族环。
8.一种三芳基硼并嘧啶高聚物,其特征在于,该高聚物的重复单元包含权利要求1-6任一项所述的三芳基硼并嘧啶化合物的结构。
9.一种权利要求1所述的三芳基硼并嘧啶化合物的应用,其特征在于,该化合物作为发光材料、发光材料、TADF主体材料和量子点主体材料。
10.一种有机电子器件,其特征在于,该有机电子器件具有电致发光功能,使用包含权利要求1-7任一项所述的三芳基硼并嘧啶化合物作为发光层材料。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211041445.5A CN115368393A (zh) | 2022-08-29 | 2022-08-29 | 一种基于三芳基硼并嘧啶有机化合物及其应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211041445.5A CN115368393A (zh) | 2022-08-29 | 2022-08-29 | 一种基于三芳基硼并嘧啶有机化合物及其应用 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN115368393A true CN115368393A (zh) | 2022-11-22 |
Family
ID=84069545
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211041445.5A Pending CN115368393A (zh) | 2022-08-29 | 2022-08-29 | 一种基于三芳基硼并嘧啶有机化合物及其应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115368393A (zh) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107793441A (zh) * | 2016-09-07 | 2018-03-13 | 学校法人关西学院 | 多环芳香族化合物 |
CN109192874A (zh) * | 2018-08-31 | 2019-01-11 | 昆山国显光电有限公司 | 一种有机电致发光器件和显示装置 |
KR20190037176A (ko) * | 2017-09-28 | 2019-04-05 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN110943176A (zh) * | 2018-09-21 | 2020-03-31 | 三星显示有限公司 | 有机发光装置及包括有机发光装置的设备 |
CN112851702A (zh) * | 2021-01-13 | 2021-05-28 | 苏州大学 | 一种有机硼化合物、聚合物、混合物及有机电子器件 |
JP2021103742A (ja) * | 2019-12-25 | 2021-07-15 | 学校法人関西学院 | 有機電界発光素子 |
CN113540371A (zh) * | 2021-06-07 | 2021-10-22 | 清华大学 | 一种有机电致发光器件和显示装置 |
CN114763361A (zh) * | 2021-01-13 | 2022-07-19 | 浙江光昊光电科技有限公司 | 一种含氮杂硼杂芘的有机化合物及其用途 |
-
2022
- 2022-08-29 CN CN202211041445.5A patent/CN115368393A/zh active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107793441A (zh) * | 2016-09-07 | 2018-03-13 | 学校法人关西学院 | 多环芳香族化合物 |
KR20190037176A (ko) * | 2017-09-28 | 2019-04-05 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN109192874A (zh) * | 2018-08-31 | 2019-01-11 | 昆山国显光电有限公司 | 一种有机电致发光器件和显示装置 |
CN110943176A (zh) * | 2018-09-21 | 2020-03-31 | 三星显示有限公司 | 有机发光装置及包括有机发光装置的设备 |
JP2021103742A (ja) * | 2019-12-25 | 2021-07-15 | 学校法人関西学院 | 有機電界発光素子 |
CN112851702A (zh) * | 2021-01-13 | 2021-05-28 | 苏州大学 | 一种有机硼化合物、聚合物、混合物及有机电子器件 |
CN114763361A (zh) * | 2021-01-13 | 2022-07-19 | 浙江光昊光电科技有限公司 | 一种含氮杂硼杂芘的有机化合物及其用途 |
CN113540371A (zh) * | 2021-06-07 | 2021-10-22 | 清华大学 | 一种有机电致发光器件和显示装置 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108727398B (zh) | 一种稠环化合物及其制备方法和用途 | |
JP6339071B2 (ja) | 有機エレクトロルミネッセンス素子のための材料 | |
CN108997347B (zh) | 一种稠环化合物及其制备方法和用途 | |
WO2022088910A1 (zh) | 一种咔唑衍生物及其应用 | |
CN108779120B (zh) | 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置 | |
CN111171038B (zh) | 一种热活化延迟荧光发射材料及其应用 | |
TW201031733A (en) | Materials for organic electroluminescent devices | |
KR20070090953A (ko) | 유기 발광 다이오드(oled)에서의 전이 금속 카르벤착체의 용도 | |
JP2013189435A (ja) | 有機エレクトロルミネセンス素子のための新規材料 | |
TW201339123A (zh) | 用於有機電致發光裝置的材料 | |
TW201024311A (en) | Materials for organic electroluminescent devices | |
TW200907016A (en) | Compound for organic electroluminescent device and organic electroluminescent device | |
CN113735855B (zh) | 一种深红/近红外光热激活延迟荧光材料及其制备方法与在有机电致发光材料中的应用 | |
CN1957018A (zh) | 电致发光聚合物 | |
CN109761879B (zh) | 有机蓝色荧光材料及其制备方法、有机电致发光器件 | |
CN112979687A (zh) | 一种热活化延迟荧光材料及其制备方法和应用 | |
Zhang et al. | Thermally activated delayed fluorescence dendrimers with AIE property and functional dendrons for high-efficiency solution-processed white OLEDs | |
CN112442046B (zh) | 萘桥联咔唑衍生物及其应用 | |
Lv et al. | Regulation of excited-state properties of dibenzothiophene-based fluorophores for realizing efficient deep-blue and HLCT-sensitized OLEDs | |
CN101550104B (zh) | 苯-萘二酰亚胺衍生物、制备方法及其应用 | |
CN110759935B (zh) | 基于氟硼络合物的蓝色热活性延迟荧光材料及其应用 | |
CN115368393A (zh) | 一种基于三芳基硼并嘧啶有机化合物及其应用 | |
CN113861206B (zh) | 一种蓝色电致发光材料及其合成方法和应用 | |
CN113735912B (zh) | 基于芳香胺类给体取代苯的给-受体型四齿环金属铂或钯配合物磷光材料及其应用 | |
WO2022088460A1 (zh) | 一种有机化合物、有机电致发光材料及有机电致发光元件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |