CN112851702B - Organic boron compound, polymer, mixture and organic electronic device - Google Patents
Organic boron compound, polymer, mixture and organic electronic device Download PDFInfo
- Publication number
- CN112851702B CN112851702B CN202110043052.7A CN202110043052A CN112851702B CN 112851702 B CN112851702 B CN 112851702B CN 202110043052 A CN202110043052 A CN 202110043052A CN 112851702 B CN112851702 B CN 112851702B
- Authority
- CN
- China
- Prior art keywords
- organoboron
- organic
- compound
- polymer
- group
- 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.)
- Active
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 150000001639 boron compounds Chemical class 0.000 title abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 230000000903 blocking effect Effects 0.000 claims description 23
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- 239000011368 organic material Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 43
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000376 reactant Substances 0.000 description 21
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000000758 substrate Substances 0.000 description 14
- -1 cyano, carbamoyl Chemical group 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WYSBZCPNRXECEW-UHFFFAOYSA-N 1-diazo-2H-anthracene Chemical compound C1=CC=C2C=C3C(=[N+]=[N-])CC=CC3=CC2=C1 WYSBZCPNRXECEW-UHFFFAOYSA-N 0.000 description 2
- YDLFYFXTJGGZLU-UHFFFAOYSA-N 1-fluoro-2,3,4-trimethylbenzene Chemical compound CC1=CC=C(F)C(C)=C1C YDLFYFXTJGGZLU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- 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
- 108010021119 Trichosanthin Proteins 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 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
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000005067 haloformyl group Chemical group 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000001755 magnetron sputter deposition Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 125000006413 ring segment Chemical group 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
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- OSEKAOVKCSZPNM-UHFFFAOYSA-N 1,3-benzoxazole;1,3-oxazole Chemical compound C1=COC=N1.C1=CC=C2OC=NC2=C1 OSEKAOVKCSZPNM-UHFFFAOYSA-N 0.000 description 1
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-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
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-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
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 description 1
- FCTIZUUFUMDWEH-UHFFFAOYSA-N 1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC=N3)C3=NC2=C1 FCTIZUUFUMDWEH-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 229910016036 BaF 2 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
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 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
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 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
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-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
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- VINBVOMNIBDIPH-UHFFFAOYSA-N isocyanoimino(oxo)methane Chemical compound O=C=N[N+]#[C-] VINBVOMNIBDIPH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000007246 mechanism Effects 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
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000002360 preparation method Methods 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
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 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
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-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
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000006617 triphenylamine group Chemical group 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
- 239000011787 zinc oxide Substances 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
-
- 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
- H10K85/10—Organic polymers or oligomers
-
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organoboron compound, a polymer, a mixture and an organic electronic device, wherein the organoboron compound comprises compounds represented by the following general formulas (1), (2), (3), (4), (5) and (6):
wherein Ar is 1 ～Ar 5 Having substituents R on the radicals 1 。Ar 1 ～Ar 5 Group A 1 ～A 5 Radicals and R 1 The groups are as defined in the specification. The organic boron compound, the polymer and the mixture have excellent luminescence performance, can be used as materials of organic material layers of organic light-emitting devices, particularly materials of core luminescent layers, and realize high efficiency and high color purity of organic light-emitting diode devices.
Description
Technical Field
The present invention relates to the field of electroluminescence, and in particular to organoboron compounds, polymers, mixtures and organic electronic devices.
Background
The organic luminescent material is easy to synthesize, easy to derive, excellent in photoelectric property and the like, so that the Organic Light Emitting Diode (OLED) has great application value and commercial potential in the fields of illumination, display and the like. Recently developed Thermally Activated Delayed Fluorescence (TADF) materials are capable of achieving both singlet exciton and triplet exciton utilization in pure organic systems free of heavy metal elements. Currently, most TADF luminescent materials are composed of an electron donor (D) and an electron acceptor (a) by single bond connection. The degree of overlap of the highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) electron clouds is smaller and the singlet energy difference is smaller. The spectrum of most TADF luminescent materials causes a problem of wider half-width due to a more distorted structure.
Disclosure of Invention
An organic boron compound, the structure of which is shown as general formulas (1), (2), (3), (4), (5) and (6):
wherein Ar is 1 ～Ar 5 The radicals being identical or different, the Ar 1 ～Ar 5 Each independently selected from any one of the aromatic, heteroaromatic or non-aromatic ring systems of 2 to 30 carbon atoms;
the Ar is as follows 1 ～Ar 5 Having R in the ring of the radical 1 A group, R 1 The radicals are identical or different on each occurrence; the R is 1 The group is selected from one or more of H, D, straight chain alkanes having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, thioalkoxy group having 1 to 20 carbon atoms, branched chain having 3 to 20 carbon atoms, cyclic alkyl having 3 to 20 carbon atoms, silyl group having 3 to 20 carbon atoms, keto group having 1 to 20 carbon atoms, alkoxycarbonyl group having 2 to 20 carbon atoms, arylcarbonyl group having 7 to 20 carbon atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, ester group, trifluoromethyl group, cl, br, I, F, crosslinkable group, substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, substituted or unsubstituted aryloxy or heteroaryloxy group having 5 to 40 ring atoms;
A 1 ～A 5 the radicals are identical or different, the A 1 ～A 5 Each group is independently a single bond or a double bridge.
An organoboron polymer, said polymer comprising at least one repeating unit comprising an organoboron compound as described above.
An organoboron mixture comprising an organoboron compound as described above or an organoboron polymer as described above, and at least one organic functional material selected from the group consisting of a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting material, and a host material.
An organic electronic device comprising a light-emitting layer made of any one of the above organoboron compounds, organoboron polymers, or organoboron mixtures.
The organic boron compound and the organic boron polymer adopt a plurality of bridge bonds to bond aromatic amine groups and organic boron groups, so that the molecular rigidity is greatly improved; meanwhile, the singlet energy gaps of the molecules are matched, so that utilization of triplet excitons can be realized, and higher color purity and high-efficiency electroluminescence can be realized. And the adjustment of the luminescence wavelength from blue light to red light can be realized through the change of the conjugated unit and the bridge bond. Thereby facilitating application on the display.
The details of one or more embodiments of the invention are set forth in the accompanying drawings and the description below. Other features, objects, and advantages of the invention will be apparent from the description and drawings, and from the claims.
Drawings
FIG. 1 is a structural general formula of an organoboron compound of the present invention;
FIG. 2 is a normalized electroluminescent spectrum of examples 47 and 48;
fig. 3 is a schematic view showing the structure of the devices of examples 47 to 53.
Wherein, the liquid crystal display device comprises a liquid crystal display device,
1: substrate and positive electrode
2: hole injection layer
3: hole transport layer
4: electron blocking layer
5: light-emitting layer
6: exciton blocking layer
7: electron transport layer
8: electron injection layer
9: negative electrode
Detailed Description
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The structure of the organoboron compound of an embodiment is shown in general formulas (1), (2), (3), (4), (5) and (6):
wherein Ar is 1 ～Ar 5 Identical or different Ar 1 ～Ar 5 Independently selected from aromatic, heteroaromatic or non-aromatic ring systems of 2 to 30 carbon atoms; ar (Ar) 1 ～Ar 5 Having a group R on the ring 1 The R is 1 The same or different at each occurrence.
A 1 ～A 5 Identical or different, independently selected from single bonds, double bonds, A 1 ～A 5 The groups adjacent thereto are independently linked by a single bond or a double bond.
R 1 Selected from H, D, straight-chain alkanes having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, thioalkoxy having 1 to 20 carbon atoms, branched having 3 to 20 carbon atoms, cyclic alkyl having 3 to 20 carbon atoms, silyl having 3 to 20 carbon atoms, keto having 1 to 20 carbon atoms, alkoxycarbonyl having 2 to 20 carbon atoms, arylcarbonyl having 7 to 20 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, ester, trifluoromethyl, cl, br, I, F, crosslinkable, substituted or unsubstituted aromatic or heteroaromatic ring systems having 5 to 40 ring atomsOne or more of substituted aryloxy or heteroaryloxy groups.
In one embodiment, according to the compounds of the invention, ar 1 ～Ar 5 Each independently comprising at least one group of the structure:
wherein:
x is a plurality of groups, each X is independently selected from N or CR 2 。
Y being plural in the same group, each Y being independently selected from CR 3 R 4 ，SiR 3 R 4 ，NR 3 ，BR 3 ，C(＝O)，S(＝O)，S(＝O) 2 S or O; r is R 2 、R 3 、R 4 Is defined as R 1 。
In one embodiment, ar 1 ～Ar 5 Each independently selected from the following groups:
in one embodiment, ar 1 ～Ar 5 Each independently selected from the following groups:
in one embodiment, ar 1 ～Ar 5 Each independently selected from the following groups:
wherein the dotted line represents a bond to an adjacent group.
In one embodiment, A 1 ～A 5 Identical or at each occurrenceThe difference is a single bond or a two-bridge bond.
In one embodiment, the two-bridge is selected from the following groups:
wherein Ar is 6 、Ar 7 With Ar as described above 1 ～Ar 5 The definition is the same; the dashed line represents a bond to an adjacent group.
In one embodiment, A 1 ～A 5 Each independently selected from the following groups:
in one embodiment, the H atom or bridging group CH on NH in the organoboron compound 2 Can be R 1 And (3) group substitution. R is R 1 The group may be selected from alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms or aryl or heteroaryl groups having 2 to 10 carbon atoms. Wherein the alkyl group having 1 to 20 carbon atoms may be selected from methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl. The alkoxy group having 1 to 10 carbon atoms may be selected from methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or 2-methylbutoxy. Aryl or heteroaryl having from 2 to 20 carbon atoms can be monovalent or divalent, depending on the application, and can in each case also be referred to as radicals R 1 Substituted and can pass through anyWhere desired is attached to an aromatic or heteroaromatic ring. Further, the method comprises the steps of, aryl or heteroaryl groups having 2 to 20 carbon atoms may be selected from benzene, naphthalene, anthracene, perylene, dihydropyrene, chrysene, perylene, fluoranthene, butazone, pentalene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzofuran, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthymidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole benzoxazole, naphthoxazole, anthracenoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, diazoanthracene, 1, 5-diazoanthracene, azacarbazole, benzocarboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazole, pteridine, and the like, indolizine or benzothiadiazole.
In a particularly preferred embodiment, ar 1 ～Ar 3 Is phenyl. B is located para to the bridged triphenylamine group, and the compound according to the present invention has one of the following formulas:
wherein the symbol definition is the same as the definition above. The benzene ring in the general formula has a group R 1 The R is 1 The same or different at each occurrence.
In a more preferred embodiment, the organoboron compound according to the invention is at least partially deuterated, preferably 10% H deuterated, more preferably 20% H deuterated, most preferably 30% H deuterated, most preferably 40% H deuterated.
The invention also relates to an organoboron high polymer, the repeating unit of which comprises the structure of the organoboron organic compound.
In certain embodiments, the organoboron high polymer is a non-conjugated high polymer. The structural unit shown in the general formula (1) is contained on a side chain. In other embodiments, the organoboron high polymer is a conjugated high polymer.
In a preferred embodiment, the organoboron polymers according to the invention have a molecular weight distribution (PDI) in the range from 1 to 5, preferably from 1 to 3, more preferably from 1 to 2, most preferably from 1 to 1.5.
In a preferred embodiment, the weight average molecular weight of the organoboron high polymer according to the present invention ranges from 1 to 100, preferably from 5 to 50, more preferably from 10 to 40, and most preferably from 20 to 25.
The organoboron polymers described above can be used in organic functional materials. The organoboron organic compounds described above may also find application in organic electronic devices.
The organoboron compound according to the invention can be applied as a functional material to organic electronic devices, in particular OLED devices. The organic functional material may be classified into a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, an electron blocking material, a hole blocking material, a light emitting material, a host material, and an organic dye.
In a preferred embodiment, the organoboron compound according to the present invention may be used as a light-emitting guest material.
In certain embodiments, the organoboron compounds according to the present invention have a luminescent function at wavelengths between 300-780nm, preferably 400-680nm, more preferably 460-630nm. Luminescence here refers to electroluminescence or photoluminescence. Further, the organoboron compound according to the present invention can be used as a light-emitting material.
The following list is given as preferred organoboron compounds, but not limited thereto, all possible substitution sites on these structures may be substituted.
In one embodiment, the organoboron compound according to the invention is a small molecule material. Thus, the organic boron compound is more suitable for evaporation type OLED. Wherein in one embodiment, the organoboron compound of the present invention has a molecular weight of 1500 g/mol or less. Further, the organoboron compound of the present invention has a molecular weight of 900 g/mol or less. Still further, the organoboron compound of the present invention has a molecular weight of 800 g/mol or less. Still further, the organoboron compound of the present invention has a molecular weight of 800 g/mol or less.
In one embodiment, the organoboron compound has a molecular weight of 700 g/mol or greater, thereby making the organoboron compound more suitable for use in printed OLEDs. Further, the molecular weight of the organoboron compound is 800 g/mol or more. Further, the molecular weight of the organoboron compound is 900 g/mol or more. Further, the molecular weight of the organoboron compound is 1000 g/mol or more. Further, the molecular weight of the organoboron compound is 1500 g/mol or more.
Based on the above-mentioned organoboron-containing compound, the present invention also provides an application of the organoboron-containing compound as described above to an organic electronic device comprising (but not limited to): organic Light Emitting Diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEEC), organic Field Effect Transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronics devices, organic sensors, organic plasma primitive light emitting diodes, and the like. Particularly preferred are organic electroluminescent devices such as organic light emitting diodes, organic lasers, organic light emitting batteries.
In certain particularly preferred embodiments, the organic electroluminescent device comprises a light-emitting layer comprising one of the organoboron compounds, or comprising one of the organoboron compounds and one of the phosphorescent emitters, or comprising one of the organoboron compounds and one of the TADF emitters, or comprising one of the organoboron compounds and one of the fluorescent emitters, or comprising one of the organoboron compounds and one of the host materials, or comprising one of the organoboron compounds, one of the phosphorescent emitters and one of the host materials, or comprising one of the organoboron compounds, one of the TADF emitters and one of the host materials.
In certain particularly preferred embodiments, the organic electroluminescent device comprises a light-emitting layer comprising one of the organoboron polymers, or comprising one of the organoboron polymers and one of the phosphorescent emitters, or comprising one of the organoboron polymers and one of the TADF emitters, or comprising one of the organoboron polymers and one of the fluorescent emitters, or comprising one of the organoboron polymers and one of the host materials, or comprising one of the organoboron polymers, one of the phosphorescent emitters and one of the host materials, or comprising one of the organoboron polymers, one of the TADF emitters and one of the host materials.
The electroluminescent device, especially the OLED, comprises a substrate, an anode, at least one light emitting layer, and a cathode.
The substrate may be transparent, opaque, partially transparent. A transparent substrate may be used to fabricate a transparent light emitting device. The substrate may be rigid or flexible. The substrate may be made of plastic, metal, semiconductor wafer, glass or their composite materials. Preferably, the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice. In a preferred embodimentThe substrate is flexible, optionally in the form of a polymer film or plastic, and has a glass transition temperature (T g ) It is 150℃or higher, preferably 200℃or higher, more preferably 300℃or higher, and most preferably 350℃or higher.
Examples of suitable flexible substrates are, but are not limited to, poly (ethylene terephthalate) (PET) and polyethylene glycol (2, 6-naphthalene) (PEN).
The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer or the hole transport layer or the light emitting layer. In one embodiment the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or of the p-type semiconductor material as hole injection layer or hole transport layer or electron blocking layer is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2eV. Examples of anode materials include (but are not limited to): al, cu, au, A, mg, fe, co, ni, mn, pd, pt, ITO aluminum-doped zinc oxide, alloys of the above examples, and the like. Other alloys of anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material may be deposited by any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam, and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and used to make the devices of the present invention.
The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the electron injection layer or the electron transport layer or the light emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO or conduction band level of the n-type semiconductor of the light-emitting or electron injection or electron transport or hole blocking layer in the light-emitting layer is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. In principle all cathode materials which can be used in OLED devices are possible as cathode materials according to the invention. Examples of cathode materials include (but are not limited to): al, au, ag, ca, ba, mg, liF/Al, mgAg alloy and BaF 2 /Al, cu, fe, co, ni, mn, pd, pt, ITO, etc. Cathode materialAny suitable technique may be selected for deposition, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam, and the like.
The OLED may also comprise other functional layers such as hole injection layers, hole transport layers, electron blocking layers, electron injection layers, electron transport layers, hole blocking layers. Materials suitable for use as these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which are hereby incorporated by reference.
An embodiment of the organoboron mixture includes at least one organofunctional material and the organoboron compound or organoboron polymer described above. In one embodiment, the organic functional material is selected from a hole injection material, a hole transport material, a hole blocking material, an electron injection material, an electron blocking material, an electron transport material, an organic light emitting material, an organic host material, or a light emitting material.
The invention also relates to the use of an organic electronic device according to the invention in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.
The invention also relates to applications of the organic electronic device according to the invention in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.
The present invention will be described with reference to preferred embodiments, but the present invention is not limited to the embodiments described below. It is to be understood that the appended claims outline the scope of the invention. It will be appreciated by those skilled in the art that certain changes may be made to the embodiments of the invention in light of the above teachings which are to be covered by the spirit and scope of the appended claims.
Example 1
2.05g of Compound A, 1.00g of Compound B, 0 are reacted under nitrogen.04g of copper powder, 3.32g of potassium carbonate, 0.16g of 18-crown-6 and 100mL of o-dichlorobenzene are reacted at 180℃with stirring for 3 days. After the reaction is finished, the temperature is reduced to room temperature, the reaction system is decompressed and filtered, and a filter cake is washed by methylene dichloride, so that a filtrate is obtained. The filtrate was distilled off under reduced pressure to remove methylene chloride and o-dichlorobenzene to obtain a crude product. The crude product was purified by column chromatography on silica gel (dichloromethane and petroleum ether as eluent) to give 2.10g of compound C. The yield was 92%. [ M ] + ]＝380。
Examples 2 to 6
Examples 2-6 employed similar synthetic procedures to example 1, with only the reactants replaced with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral measurements and yields are now listed in the table.
Example 7
2.39g of compound D, 1.02g of compound E, 0.04g of copper powder, 3.32g of potassium carbonate, 0.16g of 18-crown-6 and 100mL of o-dichlorobenzene are reacted under nitrogen at 180℃with stirring for 3 days. After the reaction is finished, the temperature is reduced to room temperature, the reaction system is decompressed and filtered, and a filter cake is washed by methylene dichloride, so that a filtrate is obtained. The filtrate was distilled off under reduced pressure to remove methylene chloride and o-dichlorobenzene to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluting with methylene chloride and petroleum ether) to give 2.30g of compound F. The yield thereof was found to be 87%. [ M ] + ]＝440。
Examples 8 to 13
Examples 8-13 employed similar synthetic procedures to example 7, with only the reactants replaced with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral measurements and yields are now listed in the table.
Example 14
5.5mL of phenylmagnesium bromide (2.2M in diethyl ether) was placed in 40mL of anhydrous, anaerobic tetrahydrofuran solution under nitrogen and stirred in a-30℃low temperature bath for 10 minutes. After 1.52G of Compound G was added to the reaction system, the reaction system was allowed to react at room temperature for 12 hours. After the reaction was completed, the reaction was quenched with a small amount of water. The reaction system was suction filtered under reduced pressure, and the filter cake was washed with ethanol. The filter cake was dried and placed in 100mL of glacial acetic acid, and a catalytic amount of concentrated hydrochloric acid was added. The reaction system was heated to 110℃and reacted for 6 hours. After the reaction was completed, the temperature was lowered to room temperature. The reaction system was poured into 500mL of ice water. And (5) carrying out vacuum filtration to obtain a filter cake. The crude product was purified by column chromatography on silica gel (dichloromethane and petroleum ether as eluent) to give 1.5g of compound H. The yield was 77%. [ M ] + ]＝486。
Examples 15 to 19
Examples 15-19 employed similar synthetic procedures to example 14, with only the reactants replaced with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral measurements and yields are now listed in the table.
Example 20
10.9mL of phenylmagnesium bromide (2.2M in diethyl ether) was placed in 60mL of anhydrous, anaerobic tetrahydrofuran solution under nitrogen and stirred in a low temperature bath at-30℃for 10 minutes. After 1.75g of the compound I was added to the reaction system, the reaction system was allowed to react at room temperature for 12 hours. After the reaction was completed, the reaction was quenched with a small amount of water. The reaction system was suction filtered under reduced pressure, and the filter cake was washed with ethanol. The filter cake was dried and placed in 100mL of glacial acetic acid, and a catalytic amount of concentrated hydrochloric acid was added. The reaction system was heated to 110℃and reacted for 6 hours. After the reaction was completed, the temperature was lowered to room temperature. The reaction system was poured into 500mL of ice water. And (5) carrying out vacuum filtration to obtain a filter cake. The crude product was purified by column chromatography on silica gel (dichloromethane and petroleum ether as eluent) to give 2.2g of compound J. The yield was 85%. [ M ] + ]＝650。
Examples 21 to 26
Examples 21-26 employed similar synthetic procedures to example 20 with only the reactants replaced with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral measurements and yields are now listed in the table.
Example 27
1.00g of Compound K was placed in 30mL of anhydrous, oxygen-free tetrahydrofuran under nitrogen and stirred in a-78℃low temperature bath for 10 minutes. 1.1mL (2.2M in tetrahydrochysene) was added dropwiseIn furan solution), the reaction system is further placed at-78 ℃ for reaction for 1 hour. After 0.78g of boron bis (trimethylphenyl) fluoride was added, the reaction system was allowed to react at room temperature for 12 hours. After the reaction was completed, a small amount of water was added to quench the reaction. The reaction system was distilled under reduced pressure to obtain a crude product, which was purified by a silica gel column (eluting solvent was methylene chloride and petroleum ether) to obtain 0.9g of compound L. The yield was 67%. [ M ] + ]＝655。
Examples 28 to 33
Examples 28-33 employed similar synthetic procedures to example 27, substituting only the reactants with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral measurements and yields are now listed in the table.
Example 34
1.00g of Compound M was placed in 30mL of anhydrous anaerobic tetrahydrofuran solution under nitrogen protection and stirred in a low temperature bath at-78℃for 10 minutes. 0.8mL (2.2M) of n-butyllithium was added dropwise, and the reaction system was allowed to react at-78℃for 1 hour. After 0.58g of boron bis (trimethylphenyl) fluoride was added, the reaction system was allowed to react at room temperature for 12 hours. After the reaction was completed, a small amount of water was added to quench the reaction. The reaction system was distilled under reduced pressure to obtain a crude product, which was purified by a silica gel column (eluting solvent was methylene chloride and petroleum ether) to obtain 0.7g of compound N. The yield was 56%. [ M ] + ]＝819。
Examples 35 to 40
Examples 35-40 employed similar synthetic procedures to example 34 with only the reactants replaced with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral measurements and yields are now listed in the table.
Example 41
1.0g of compound O, 0.2g of compound P, 0.1g of tris (dibenzylideneacetone) dipalladium, 0.8g of sodium tert-butoxide, 0.06g of tri-tert-butylphosphine tetrafluoroborate and 30mL of toluene are heated to 110℃under stirring under nitrogen for 12 hours. After the reaction was completed, the temperature was lowered to room temperature. The reaction was filtered through celite under reduced pressure, and the celite was rinsed with dichloromethane. The organic liquid phase was concentrated by distillation under reduced pressure to give a crude product, which was purified by a silica gel column (eluent dichloromethane and petroleum ether) to give 0.8g of compound Q. The yield was 78%. [ M ] + ]＝473。
1.0g of compound Q, 0.68g of compound R, 0.13g of copper powder, 0.06g of 18-crown-6, 0.44g of potassium carbonate and 30mL of o-dichlorobenzene are heated to 180 ℃ with stirring under nitrogen protection and reacted for 72 hours. After the reaction was completed, the temperature was lowered to room temperature. The reaction system was filtered under reduced pressure and rinsed with dichloromethane. The organic liquid phase was concentrated by distillation under reduced pressure to give a crude product, which was purified by a silica gel column (eluent dichloromethane and petroleum ether) to give 0.92g of compound S. The yield was 65%. [ M ] + ]＝666。
1.0g of Compound S was dissolved in 20mL of tetrahydrofuran under nitrogen. It was added to 4.1mL (2.2M) of methylmagnesium bromide at-78deg.C. After stirring for 10 minutes, the reaction system was set upThe reaction was continued for 6 hours at room temperature. After the reaction was completed, a small amount of water was added to quench the reaction. The reaction system is decompressed, pumped, filtered and removed the solvent to obtain the intermediate. The intermediate is dissolved in 100mL of glacial acetic acid after being dried in vacuum, stirred and heated to 110 ℃, and then a catalytic amount of concentrated hydrochloric acid is added for continuous reaction for 6 hours. After the reaction was completed, the temperature was lowered to room temperature. The reaction system was poured into ice water. The crude product was obtained after suction filtration under reduced pressure and purified by a silica gel column (dichloromethane and petroleum ether as eluent) to give 0.4g of compound T. The yield was 40%. [ M ] + ]＝666。
Examples 42 to 46
Examples 42-46 employed similar synthetic procedures to example 41, with only the reactants replaced with the corresponding reactants. The corresponding reactants and target products and the corresponding mass spectral detection values are now listed in the table.
Because a plurality of bridging bonds exist in the organic boron derivative, the molecule has stronger rigidity and can have narrower luminescence spectrum; meanwhile, due to the fact that the material has a heat-activated delayed fluorescence luminescence mechanism, the maximum external quantum efficiency of more than 5% can be achieved in the electroluminescent device, and meanwhile, the luminescent color purity of the electroluminescent device is high (the half-peak width of a spectrum is less than 80 nm) due to the fact that the material is of a relatively rigid molecular structure.
The invention also provides an organic electroluminescent device prepared based on the organic boron derivative, which comprises a cathode, an anode and an organic film layer, wherein the organic film layer is arranged between the cathode and the anode, the organic film layer comprises at least one organic light-emitting layer, and the organic film layer contains the organic boron derivative, preferably an organic light-emitting layer prepared from the organic light-emitting material.
The organic thin film layer further comprises a hole injection layer, a hole transmission layer, an electron blocking layer and an electron transmission layer, and the anode, the hole injection layer, the hole transmission layer, the electron blocking layer, the organic light emitting layer, the exciton blocking layer, the electron transmission layer, the electron injection layer and the cathode are sequentially arranged on the organic electroluminescent device from the height direction.
Next, the organic electroluminescent device of the present invention will be described.
The glass plate coated with the ITO transparent conductive layer is subjected to ultrasonic treatment in a commercial cleaning agent, rinsed in deionized water, respectively cleaned three times in acetone and ethanol, baked in a clean environment until the water is completely removed, cleaned by ultraviolet light and ozone, and bombarded on the surface by a low-energy cation beam. Placing ITO conductive glass into vacuum chamber, vacuumizing to below 5×10 -4 Pa. Taking ITO conductive glass as an anode, and sequentially evaporating a Hole Injection Layer (HIL), a hole transport layer (HIL), an Electron Blocking Layer (EBL), an organic light emitting layer (EML), an Electron Transport Layer (ETL) and a cathode on the ITO conductive glass; wherein, the evaporation rate of the organic material is 0.2nm/s, and the evaporation rate of the metal electrode is 0.5nm/s.
The electroluminescent spectra were collected using a photon multichannel analyzer PMA-12 (Hamamatsu C10027-01) which can be detected in the spectral region of 200-950 nm. The external quantum efficiency of the device was obtained by measuring the forward light intensity using an integrating sphere (Hamamatsu a 10094). All measurements were performed at room temperature under atmospheric conditions.
The method for forming each structural layer in the organic electroluminescent device of the present invention is not particularly limited, and may use a conventional vacuum evaporation method, spin coating method, or the like; meanwhile, the materials used for each structural layer in the electroluminescent device of the present invention are not particularly limited as well, and the device structure in the examples is merely to illustrate the characteristics of the organoboron derivative of the present invention.
Example 47
The compound of the present invention is purified by sublimation in high purity by the existing method, and then an organic light emitting device is manufactured by the following method.
Will be thinly coatedIs coated with a thickness of
The glass substrate of Indium Tin Oxide (ITO) was put into distilled water in which a cleaning agent was dissolved and subjected to ultrasonic washing. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes, and then ultrasonic washing was performed with isopropanol, acetone, and methanol solvents, and drying was performed. The substrate is then transferred to a plasma cleaner. In addition, the substrate was cleaned using oxygen plasma for 6 minutes, and then transferred to a vacuum evaporator.
2,3,6,7, 10, 11-hexacyano-1,4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN) of the following chemical formula was thermally and vacuum-on the transparent ITO electrode thus prepared to a thickness of
As a hole injection layer.
The following compound 4,4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline was used as a material for transporting holes](TAPC)
Vacuum deposition is performed on the hole injection layer, thereby forming a hole transport layer.
Subsequently, the following compound 1, 3-di-9-carbazolylbenzene (mCP) as a material for electron blocking was allowed to occur
Vacuum deposition onAn electron blocking layer is formed on the hole transport layer. />
Then, the following compound 1 and bis [2- ((oxo) diphenylphosphino) phenyl]Ether (DPEPO) was vacuum deposited on the electron blocking layer in a weight ratio of 2:8 to a thickness of
Thereby forming a light emitting layer.
Then, the following bis [2- ((oxo) diphenylphosphino) phenyl group]Ether (DPEPO) is deposited on the luminescent layer in vacuum with a thickness of
Thereby forming an exciton blocking layer.
The following electron-transporting materials 1,3, 5-tris [ (3-pyridyl) -3-phenyl ]]Benzene (TmPyPB)
Vacuum deposited on the light-emitting layer with a thickness of +.>
An electron transport layer is formed.
The compound lithium 8-hydroxyquinoline (Liq)
And metallic aluminum->
Sequentially deposited on the electron transport layer as an electron injection layer and a cathode.
In the above process, the deposition rates of the hole injection layer material HAT-CN and the electron injection layer material Liq are kept at
To->
The deposition rate of the organic functional layer material including hole transport layer material, electron blocking layer material, luminescent layer material, electron transport layer material is maintained at +.>
To->
The deposition rate of the electrode material metallic aluminium is kept +.>
To->
And the vacuum degree during deposition is maintained at 1×10 -7 To 5X 10 -6 The support, thereby manufacturing the organic light emitting device.
Examples 48 to 53
Examples 48 to 53 use the same preparation conditions and processes as in example 47, except that compound 1 of the light-emitting layer was replaced with the corresponding organoboron derivative of the present invention. The corresponding compounds and corresponding device parameters are now listed in the table.
From examples 47 to 53, it is understood that the organoboron compound of the present invention can achieve high efficiency and high color purity in an electroluminescent device.
The technical features of the above-described exemplary embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described exemplary embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be regarded as the scope of the description of the present specification.
The above-described exemplary embodiments represent only a few embodiments of the present invention, which are described in more detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (5)
1. An organoboron compound, characterized in that the organoboron compound is selected from any one of the following:
or (b)
。
2. An organoboron polymer comprising the organoboron compound of claim 1, wherein the repeating units of the organoboron polymer comprise an organoboron compound of the organoboron polymer.
3. An organoboron mixture comprising the organoboron compound of claim 1 or the organoboron polymer of claim 2, and at least one organic functional material selected from the group consisting of a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting material, and a host material.
4. An organic electronic device comprising the organoboron compound of claim 1 or the organoboron polymer of claim 2 or the organoboron mixture of claim 3.
5. The organic electronic device of claim 4, wherein the organic electronic device has a light-emitting layer made of any one of the organoboron compound, the organoboron polymer, or the organoboron mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110043052.7A CN112851702B (en) | 2021-01-13 | 2021-01-13 | Organic boron compound, polymer, mixture and organic electronic device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110043052.7A CN112851702B (en) | 2021-01-13 | 2021-01-13 | Organic boron compound, polymer, mixture and organic electronic device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112851702A CN112851702A (en) | 2021-05-28 |
| CN112851702B true CN112851702B (en) | 2023-04-28 |
Family
ID=76003390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110043052.7A Active CN112851702B (en) | 2021-01-13 | 2021-01-13 | Organic boron compound, polymer, mixture and organic electronic device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112851702B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113788851A (en) * | 2021-08-09 | 2021-12-14 | 深圳大学 | Halogenated polycyclic aromatic compound containing boron atom and preparation method thereof |
| CN115368393A (en) * | 2022-08-29 | 2022-11-22 | 哈尔滨工业大学 | Triaryl-based boraopyrimidine organic compound and application thereof |
| CN116478182B (en) * | 2023-03-13 | 2024-03-29 | 华南理工大学 | Units based on bridged triphenylamine derivatives, small molecules and polymers containing units, and preparation methods and applications thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018783A (en) * | 2019-11-05 | 2020-04-17 | 苏州久显新材料有限公司 | Spirobenzanthrone derivatives and electronic devices |
-
2021
- 2021-01-13 CN CN202110043052.7A patent/CN112851702B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN112851702A (en) | 2021-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102627527B1 (en) | Material for organic electroluminescent devices | |
| JP5677983B2 (en) | Organic electronic devices | |
| JP6396446B2 (en) | Polycyclic compound | |
| US9017825B2 (en) | Anthracene derivatives and their use in organic electroluminescent devices | |
| CN107635987B (en) | Material for organic electroluminescent device | |
| JP6576915B2 (en) | Boron-containing compounds for use in OLEDs | |
| KR101410190B1 (en) | New materials for organic electroluminescent devices | |
| JP5280374B2 (en) | Novel materials for organic electroluminescent devices | |
| JP5726734B2 (en) | Compounds for electronic devices | |
| CN112851702B (en) | Organic boron compound, polymer, mixture and organic electronic device | |
| TWI510471B (en) | Compounds for electronic devices | |
| US20080145698A1 (en) | Compounds For Organic Electronic Devices | |
| JP6749913B2 (en) | Carbazole with two dibenzofuran or dibenzothiophene substituents | |
| KR20110122129A (en) | Materials for organic electroluminescence devices | |
| KR20190100469A (en) | Materials for organic electroluminescence devices | |
| JP2007527116A (en) | Organic electronic devices | |
| KR20110122130A (en) | Materials for organic electroluminescence devices | |
| JP2008536320A (en) | Organic electroluminescence device | |
| CN111247159A (en) | Transition metal complex material and application thereof in electronic device | |
| CN110981895A (en) | Transition metal complexes, polymers, mixtures, compositions and organic electronic devices | |
| WO2019114608A1 (en) | Transition metal complex, polymer, mixture, composition and use thereof | |
| CN116406414A (en) | Heteroatom-containing compounds for organic electroluminescent devices | |
| CN113024607A (en) | Transition metal complexes, polymers, mixtures, compositions and organic electronic devices | |
| CN111278836A (en) | Metal organic complex and application thereof in organic electronic device | |
| CN112940016B (en) | Transition metal complexes, mixtures, compositions and organic electronic devices |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |