CN114031975A - Composition, quantum dot ink and quantum dot light-emitting device - Google Patents
Composition, quantum dot ink and quantum dot light-emitting device Download PDFInfo
- Publication number
- CN114031975A CN114031975A CN202011201307.XA CN202011201307A CN114031975A CN 114031975 A CN114031975 A CN 114031975A CN 202011201307 A CN202011201307 A CN 202011201307A CN 114031975 A CN114031975 A CN 114031975A
- Authority
- CN
- China
- Prior art keywords
- group
- atoms
- quantum dot
- substituted
- ring atoms
- 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
- 239000002096 quantum dot Substances 0.000 title claims abstract description 123
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 229910052796 boron Inorganic materials 0.000 claims abstract description 29
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 alkane thioether Chemical class 0.000 claims description 96
- 125000006413 ring segment Chemical group 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000003254 radicals Chemical group 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000005067 haloformyl group Chemical group 0.000 claims description 7
- 239000002346 layers by function Substances 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 5
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 150000008365 aromatic ketones Chemical class 0.000 claims description 4
- 150000008378 aryl ethers Chemical class 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002485 inorganic esters Chemical class 0.000 claims description 3
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910017115 AlSb Inorganic materials 0.000 claims description 2
- 229910004613 CdTe Inorganic materials 0.000 claims description 2
- 229910005540 GaP Inorganic materials 0.000 claims description 2
- 229910005542 GaSb Inorganic materials 0.000 claims description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 claims description 2
- 229910000530 Gallium indium arsenide Inorganic materials 0.000 claims description 2
- 229910004262 HgTe Inorganic materials 0.000 claims description 2
- 229910000673 Indium arsenide Inorganic materials 0.000 claims description 2
- 229910007709 ZnTe Inorganic materials 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- WPYVAWXEWQSOGY-UHFFFAOYSA-N indium antimonide Chemical compound [Sb]#[In] WPYVAWXEWQSOGY-UHFFFAOYSA-N 0.000 claims description 2
- RPQDHPTXJYYUPQ-UHFFFAOYSA-N indium arsenide Chemical compound [In]#[As] RPQDHPTXJYYUPQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 239000000976 ink Substances 0.000 description 67
- 238000007639 printing Methods 0.000 description 25
- 239000010410 layer Substances 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 238000007641 inkjet printing Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- NNWHUJCUHAELCL-SNAWJCMRSA-N trans-isomethyleugenol Chemical compound COC1=CC=C(\C=C\C)C=C1OC NNWHUJCUHAELCL-SNAWJCMRSA-N 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- PBCTYXBHPFCNBB-UHFFFAOYSA-N 2-phenoxyoxolane Chemical compound C1CCOC1OC1=CC=CC=C1 PBCTYXBHPFCNBB-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 2
- KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 description 2
- HJKGBRPNSJADMB-UHFFFAOYSA-N 3-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1 HJKGBRPNSJADMB-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 2
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003277 amino 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- GGBJHURWWWLEQH-UHFFFAOYSA-N butylcyclohexane Chemical compound CCCCC1CCCCC1 GGBJHURWWWLEQH-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 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 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- VINBVOMNIBDIPH-UHFFFAOYSA-N isocyanoimino(oxo)methane Chemical compound O=C=N[N+]#[C-] VINBVOMNIBDIPH-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 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
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 238000013088 quantum-dot photovoltaic Methods 0.000 description 2
- 239000004054 semiconductor nanocrystal Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 1
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- 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
- FQYVVSNFPLKMNU-UHFFFAOYSA-N 1,2-dipentylbenzene Chemical compound CCCCCC1=CC=CC=C1CCCCC FQYVVSNFPLKMNU-UHFFFAOYSA-N 0.000 description 1
- UTFRNSPYRPYKDV-UHFFFAOYSA-N 1,3-dipropoxybenzene Chemical compound CCCOC1=CC=CC(OCCC)=C1 UTFRNSPYRPYKDV-UHFFFAOYSA-N 0.000 description 1
- GWTBXGSNWKXTPX-UHFFFAOYSA-N 1,3-dipropylbenzene Chemical compound CCCC1=CC=CC(CCC)=C1 GWTBXGSNWKXTPX-UHFFFAOYSA-N 0.000 description 1
- 239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- IQISOVKPFBLQIQ-UHFFFAOYSA-N 1,4-dimethoxy-2-methylbenzene Chemical compound COC1=CC=C(OC)C(C)=C1 IQISOVKPFBLQIQ-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 1
- JRRDISHSXWGFRF-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOC JRRDISHSXWGFRF-UHFFFAOYSA-N 0.000 description 1
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 1
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- LIWRTHVZRZXVFX-UHFFFAOYSA-N 1-phenyl-3-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC(C=2C=CC=CC=2)=C1 LIWRTHVZRZXVFX-UHFFFAOYSA-N 0.000 description 1
- KWSHGRJUSUJPQD-UHFFFAOYSA-N 1-phenyl-4-propan-2-ylbenzene Chemical group C1=CC(C(C)C)=CC=C1C1=CC=CC=C1 KWSHGRJUSUJPQD-UHFFFAOYSA-N 0.000 description 1
- MCUPBIBNSTXCPQ-UHFFFAOYSA-N 1-tert-butyl-4-methoxybenzene Chemical compound COC1=CC=C(C(C)(C)C)C=C1 MCUPBIBNSTXCPQ-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
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- OITMBHSFQBJCFN-UHFFFAOYSA-N 2,5,5-trimethylcyclohexan-1-one Chemical compound CC1CCC(C)(C)CC1=O OITMBHSFQBJCFN-UHFFFAOYSA-N 0.000 description 1
- GFWVDQCGGDBTBS-UHFFFAOYSA-N 2,6,8-trimethylnonan-4-one Chemical compound CC(C)CC(C)CC(=O)CC(C)C GFWVDQCGGDBTBS-UHFFFAOYSA-N 0.000 description 1
- GUMOJENFFHZAFP-UHFFFAOYSA-N 2-Ethoxynaphthalene Chemical compound C1=CC=CC2=CC(OCC)=CC=C21 GUMOJENFFHZAFP-UHFFFAOYSA-N 0.000 description 1
- SPKSOWKQTVDRTK-UHFFFAOYSA-N 2-hydroxy-4-(4-methyl-1,3-dioxoisoindol-2-yl)benzoic acid Chemical group O=C1C=2C(C)=CC=CC=2C(=O)N1C1=CC=C(C(O)=O)C(O)=C1 SPKSOWKQTVDRTK-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- SHRDVLUJLDYXSO-UHFFFAOYSA-N 2-phenoxyoxane Chemical compound O1CCCCC1OC1=CC=CC=C1 SHRDVLUJLDYXSO-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- AQIIVEISJBBUCR-UHFFFAOYSA-N 4-(3-phenylpropyl)pyridine Chemical compound C=1C=NC=CC=1CCCC1=CC=CC=C1 AQIIVEISJBBUCR-UHFFFAOYSA-N 0.000 description 1
- SBUYFICWQNHBCM-UHFFFAOYSA-N 4-Ethyl-o-xylene Chemical compound CCC1=CC=C(C)C(C)=C1 SBUYFICWQNHBCM-UHFFFAOYSA-N 0.000 description 1
- KGYYLUNYOCBBME-UHFFFAOYSA-M 4-fluoro-2-phenyl-4-(4-propylcyclohexyl)cyclohexa-1,5-diene-1-carboxylate Chemical compound C1CC(CCC)CCC1C1(F)C=CC(C([O-])=O)=C(C=2C=CC=CC=2)C1 KGYYLUNYOCBBME-UHFFFAOYSA-M 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- UXPXQSWKWHQUCB-UHFFFAOYSA-N 5-(furan-2-yl)-1h-indole Chemical compound C1=COC(C=2C=C3C=CNC3=CC=2)=C1 UXPXQSWKWHQUCB-UHFFFAOYSA-N 0.000 description 1
- AZZHCIXSZZXEAS-UHFFFAOYSA-N 5-phenylpentylbenzene Chemical compound C=1C=CC=CC=1CCCCCC1=CC=CC=C1 AZZHCIXSZZXEAS-UHFFFAOYSA-N 0.000 description 1
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
- MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- AGUBCDYYAKENKG-UHFFFAOYSA-N Abietinsaeure-aethylester Natural products C1CC(C(C)C)=CC2=CCC3C(C(=O)OCC)(C)CCCC3(C)C21 AGUBCDYYAKENKG-UHFFFAOYSA-N 0.000 description 1
- YNMZZHPSYMOGCI-UHFFFAOYSA-N Aethyl-octyl-keton Natural products CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 229910004609 CdSn Inorganic materials 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- AGUBCDYYAKENKG-YVNJGZBMSA-N Ethyl abietate Chemical compound C1CC(C(C)C)=CC2=CC[C@H]3[C@@](C(=O)OCC)(C)CCC[C@]3(C)[C@H]21 AGUBCDYYAKENKG-YVNJGZBMSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- HDJLSECJEQSPKW-UHFFFAOYSA-N Methyl 2-Furancarboxylate Chemical compound COC(=O)C1=CC=CO1 HDJLSECJEQSPKW-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- 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
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-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
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 150000001555 benzenes Chemical class 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- ZTPZXOVJDMQVIK-UHFFFAOYSA-N dodecane-1-selenol Chemical compound CCCCCCCCCCCC[SeH] ZTPZXOVJDMQVIK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229930006735 fenchone Natural products 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
- 230000004927 fusion Effects 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 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
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 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
- 239000002086 nanomaterial Substances 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 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
- 230000003287 optical effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N p-methylisopropylbenzene Natural products CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 238000007649 pad printing Methods 0.000 description 1
- 239000002245 particle Substances 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 229930193351 phorone Natural products 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 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
- 125000000719 pyrrolidinyl group Chemical group 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
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- 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
- H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a composition, quantum dot ink and a quantum dot light-emitting device, wherein the composition comprises a quantum dot material and a boron-containing compound with a structure shown in a formula (I);the composition has excellent charge transmission capability, and the viscosity and surface tension requirements of the quantum dot ink can be met by reasonably adjusting the concentration of each component of the composition.
Description
Technical Field
The invention relates to the technical field of photoelectric materials, in particular to a composition, quantum dot ink and a quantum dot light-emitting device.
Background
At present, an Organic Light Emitting Diode (OLED) as a new generation display technology is manufactured by an evaporation method, a large number of vacuum processes are involved in the manufacturing process, the material utilization rate is low, a fine mask (FMM) is required, the cost is high, and the yield is low. In order to solve the above problems, attention is being paid to a technology for realizing high-resolution full-color display by using a printing process. For example, the ink-jet printing can prepare the functional material film in a large area and at low cost, and compared with the traditional semiconductor production process, the ink-jet printing has the advantages of low energy consumption, low water consumption, environmental friendliness and great advantages and potentials. Another new display technology, quantum dot light emitting diodes (QLEDs), cannot be vapor deposited and must be prepared by printing. Therefore, the key problems of printing ink and related printing process must be broken through to realize printing display. While viscosity and surface tension are important parameters affecting printing inks and printing processes, a promising printing ink needs to have an appropriate viscosity and surface tension.
Organic semiconducting materials have gained widespread interest and significant progress in their application in electronic and optoelectronic devices due to their solution processability. Solution processability allows organic functional materials to be formed into thin films of the functional material in devices by certain coating and printing techniques. The technology can effectively reduce the processing cost of electronic and optoelectronic devices and meet the process requirement of large-area preparation. At present, several companies have reported organic semiconductor material inks for printing, such as: KATEEVA, INC discloses an organic small molecule material ink based on ester solvents for printable OLEDs; UNIVERSAL DISPLAY CORPORATION discloses a printable ink of organic small molecule materials based on solvents of aromatic ketones or aromatic ethers; SEIKO EPSON CORPORATION discloses printable organic polymeric material inks based on substituted benzene derivative solvents.
Another class of functional materials that may be suitable for printing are inorganic nanomaterials, in particular quantum dots. Quantum dots are semiconductor materials of nanometer size having quantum confinement effect, and when stimulated by light or electricity, the quantum dots emit fluorescence with specific energy, and the color (energy) of the fluorescence is determined by the chemical composition and size and shape of the quantum dots. Therefore, the control on the size and the shape of the quantum dot can effectively regulate and control the electrical and optical properties of the quantum dot. At present, all countries research the application of quantum dots in full color, and mainly focus on the display field. Recently, the electroluminescent device (QLED) using quantum dots as the light emitting layer has been rapidly developed, and the device lifetime has been greatly improved, as reported by Peng et al in Nature Vol 51596 (2015), and Qian et al in Nature Photonics Vol 9259 (2015). Currently, several companies have reported quantum dot inks for printing: british nanotechnology Ltd (Nanoco Technologies Ltd) discloses a method of preparing a printable ink formulation comprising nanoparticles. By selecting proper solvents, such as toluene and dodecaneselenol, printable nanoparticle ink and a corresponding nanoparticle-containing film are obtained; samsung Electronics (Samsung Electronics) discloses a quantum dot ink for inkjet printing. The ink comprises a certain concentration of quantum dot material, an organic solvent and an alcohol polymer additive with high viscosity. Printing the ink to obtain a quantum dot film and prepare a quantum dot electroluminescent device; QD Vision (QD Vision, Inc.) discloses an ink formulation of quantum dots comprising a host material, a quantum dot material, and an additive (US2010264371a 1).
Other patents relating to quantum dot printing inks include: US2008277626a1, US2015079720a1, US2015075397a1, TW201340370A, US2007225402a1, US2008169753a1, US2010265307a1, US2015101665a1, WO2008105792a 2. In these published patents, the quantum dot inks contain other additives, such as alcohol polymers, in order to control the physical parameters of the inks. The introduction of polymer additives with insulating properties tends to reduce the charge transport capability of the thin film, which has a negative impact on the optoelectronic properties of the device, limiting its wide application in optoelectronic devices.
Disclosure of Invention
Based on the above, there is a need for a composition, a quantum dot ink and an application thereof in a quantum dot light emitting device, wherein the composition has excellent charge transport capability, and the viscosity and surface tension requirements of the quantum dot ink can be met by reasonably adjusting the concentrations of the components of the composition.
A composition comprising a quantum dot material and a boron-containing compound of the structure shown in formula (I);
wherein Ar is1~Ar5At each occurrence, identical or different, Ar1~Ar5Each independently selected from: a substituted or unsubstituted aryl group having 5 to 20 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms, or a substituted or unsubstituted non-aromatic group having 5 to 20 ring atoms;
and Ar is2With said Ar5Connected or not connected, Ar3With said Ar4Connected or not connected.
A quantum dot ink comprises the composition and an organic solvent.
A quantum dot light-emitting device comprises a functional layer, wherein the functional layer is mainly prepared from the quantum dot ink.
The composition is beneficial to forming excitons on the boron-containing compound by electrons and holes after a luminescent layer is formed by adopting the boron-containing compound and quantum dot material composition with the structure shown in the formula (I), and then transferring the energy of the excitons to the quantum dots for luminescence, thereby achieving the purpose of improving the charge transmission capability; the boron-containing compound and quantum dot material composition of the composition has proper solubility in most of organic solvents for ink-jet printing, and the adjustment of the viscosity and the surface tension of the quantum dot ink can be realized by adjusting the concentrations of the boron-containing compound and the quantum dot material composition in the printing ink, so that the requirement of ink-jet printing is met, the reduction of charge transmission capability caused by additives such as alcohol polymers is avoided, and the luminous efficiency of a quantum dot light-emitting device is further improved.
Drawings
Fig. 1 is a schematic view of a quantum dot light emitting device according to an embodiment of the present invention.
Detailed Description
In order that the invention may be more fully understood, a more particular description of the invention will now be rendered by reference to specific embodiments thereof that are illustrated in the appended drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
In the present invention, "substituted" means that a hydrogen atom in a substituent is substituted by a substituent.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood to be optionally substituted with art-acceptable groups including, but not limited to: c1-30Alkyl, heterocyclyl containing 3 to 20 ring atoms, aryl containing 5 to 20 ring atoms, heteroaryl containing 5 to 20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, -NRR', cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, trifluoromethyl, nitro or halogen, and the above groups may be further substituted with art-acceptable substituents; it is understood that R and R 'in-NRR' are each independently substituted with art-acceptable groups including, but not limited to, H, C1-6An alkyl group, a cycloalkyl group having 3 to 8 ring atoms, a heterocyclic group having 3 to 8 ring atoms, an aryl group having 5 to 20 ring atoms or a heteroaryl group having 5 to 10 ring atoms; said C is1-6Alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclyl containing 3 to 8 ring atoms, aryl containing 5 to 20 ring atoms or heteroaryl containing 5 to 10 ring atoms are optionally further substituted by one or more of the following: c1-6Alkyl, cycloalkyl having 3 to 8 ring atoms, heterocyclyl having 3 to 8 ring atoms, halogen, hydroxy, nitro or amino.
In the present invention, the "number of ring atoms" represents the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
In the present invention, "alkyl" may mean a linear, branched and/or cyclic alkyl group. In the present invention, the alkyl group having no specified carbon number means that an optional number may be provided, and the carbon number of the alkyl group may be 1 to 50; further, the carbon number of the alkyl group may be 1 to 30; further, the carbon number of the alkyl group may be 1 to 20; further, the carbon number of the alkyl group may be 1 to 10; further, the carbon number of the alkyl group may be 1 to 6; further, the carbon number of the alkyl group may be 1 to 4. Phrases containing the term, e.g., "C1~C9Alkyl "refers to an alkyl group containing 1 to 9 carbon atoms, which may be independently at each occurrence C1Alkyl radical, C2Alkyl radical, C3Alkyl radical, C4Alkyl radical, C5Alkyl radical, C6Alkyl radical, C7Alkyl radical, C8Alkyl or C9An alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, tert-butyl, 2-isobutyl, 2-ethylbutyl, 3-dimethylbutyl, 2-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-butylcyclohexyl, 2-butylheptyl, 2-methylheptyl, 2-ethylheptyl, 2-ethyloctyl, 2-tert-butylhexyl, 2-butylhexyl, or a, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecylA base group, a n-hexadecyl group, a 2-ethylhexadecyl group, a 2-butylhexadecyl group, a 2-hexylhexadecyl group, a 2-octylhexadecyl group, a n-heptadecyl group, a n-octadecyl group, a n-nonadecyl group, a n-eicosyl group, a 2-ethyleicosyl group, a 2-butyleicosyl group, a 2-hexyleicosyl group, a 2-octyleicosyl group, a n-heneicosyl group, a n-docosyl group, a n-tricosyl group, a n-tetracosyl group, a n-pentacosyl group, a n-hexacosyl group, a n-heptacosyl group, a n-octacosyl group, a n-nonacosyl group, a n-triacontyl group, adamantane group and the like.
"Heterocycloalkyl" means a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon substituent in which one or more ring atoms are selected from nitrogen, oxygen, or S (O)m(wherein m is an integer of 0 to 2), preferably a nitrogen or oxygen heteroatom; but not the ring moiety of-O-, -O-S-or-S-, the remaining ring atoms being carbon. 3-10 membered heterocyclyl is a ring containing 3 to 10 ring atoms, of which 1-3 are heteroatoms; preferably, the heterocyclyl ring contains from 3 to 8 ring atoms of which 1-2 are heteroatoms. In one embodiment, the monocyclic heterocyclyl is dihydrofuranyl, tetrahydrofuranyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, or homopiperazinyl, and the like.
As used herein, "fused ring" refers to polycyclic groups in which each ring in the system shares an adjacent pair of carbon atoms with other rings in the system, such as naphthyl, anthryl, phenanthryl, and the like. Fused rings optionally contain 0 or more heteroatoms, i.e., fused rings may or may not contain heteroatoms.
The term "alkoxy" refers to a group having an-O-alkyl group, i.e., an alkyl group as defined above attached to the parent core structure via an oxygen atom. Phrases encompassing this term, suitable examples include, but are not limited to: methoxy (-O-CH)3or-OMe), ethoxy (-O-CH)2CH3or-OEt) and tert-butoxy (-O-C (CH)3)3or-OtBu).
"aryl" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from the aromatic ring compound and may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for polycyclic ring species. For example, "substituted or unsubstituted aryl having 5 to 60 ring atoms" means an aryl group containing 5 to 60 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, naphthalene, anthracene, phenanthrene, perylene, triphenylene, and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. < 10% of non-H atoms, such as C, N or O atoms), such as in particular acenaphthene, fluorene, or 9, 9-diarylfluorene, triarylamine, diarylether systems should also be included in the definition of aryl groups.
"heteroaryl" means that on the basis of an aryl at least one carbon atom is replaced by a non-carbon atom which may be a N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 60 ring atoms" refers to heteroaryl having 5 to 60 ring atoms, and the heteroaryl is optionally further substituted, suitable examples include, but are not limited to: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, primadine, quinazoline, and quinazolinone.
In the present invention, m-membered aryl means aryl group containing m ring atoms, m-membered heteroaryl means heteroaryl group containing m ring atoms, for example: "5-10 membered aryl" refers to aryl groups containing 5-10 ring atoms, and "5-10 membered heteroaryl" refers to heteroaryl groups containing 5-10 ring atoms.
"amino" refers to a derivative of an amine having the formula-N (X)2Wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or the like. Non-limiting types of amine groups include-NH2-N (alkyl)2NH (alkyl), -N (cycloalkyl)2NH (cycloalkyl), -N (heterocyclyl)2-NH (heterocycle)Radical), -N (aryl)2NH (aryl), -N (alkyl) (heterocyclyl), -N (cycloalkyl) (heterocyclyl), -N (aryl) (heteroaryl), -N (alkyl) (heteroaryl), and the like.
"halogen" or "halo" refers to F, Cl, Br, or I.
"alkylamino" refers to an amino group substituted with at least one alkyl group. Suitable examples include, but are not limited to: -NH2、-NH(CH3)、-N(CH3)2、-NH(CH2CH3)、-N(CH2CH3)2。
"arylalkyl" refers to a hydrocarbyl radical derived from an alkyl radical having at least one hydrogen atom bonded to a carbon atom replaced by an aryl radical. Wherein the aryl moiety may include 5 to 20 carbon atoms and the alkyl moiety may include 1 to 9 carbon atoms. Suitable examples include, but are not limited to: benzyl, 2-phenyleth-1-yl, naphthylmethyl, 2-naphthyleth-1-yl, naphthobenzyl and 2-naphthophenyleth-1-yl.
In the present invention, "+" attached to a single bond represents a connection or a fusion site;
in the present invention, when the attachment site is not specified in the group, it means that an optional attachment site in the group is used as the attachment site;
in the present invention, when a fused site is not specified in a group, it means that an optionally fused site in the group is a fused site, and preferably two or more sites in the ortho-position in the group are fused sites;
in the context of the present invention, an atom in a group at the attachment site or the fused site also satisfies the valence of the atom, e.g.When the atom as the linking site in (1) is a tetravalent atom, no other substituent is present thereon;
in the context of the present invention, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached at an optional position on the ring, for exampleWherein R is represented byAny substitutable site of the pyridine ring is linked.
In the present invention, when the same group contains a plurality of substituents of the same symbol, the substituents may be the same or different from each other, for example6R on the benzene ring1May be the same as or different from each other.
In the present invention, when the specific number of substituents is not specified, the substituents are represented by optionally substitutable numbers, such as R0Substituted phenyl, said phenyl being optionally substituted by 1,2,3 or 4, etc. R0And (4) substitution.
Detailed Description
One embodiment of the invention provides a composition comprising a quantum dot material and a boron-containing compound having a structure represented by formula (I);
wherein Ar is1~Ar5At each occurrence, identical or different, Ar1~Ar5Each independently selected from: a substituted or unsubstituted aryl group having 5 to 20 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms, or a substituted or unsubstituted non-aromatic group having 5 to 20 ring atoms; and Ar2And Ar5Connected or disconnected, Ar3And Ar4Connected or not connected.
Further, Ar1~Ar5Each independently selected from: a substituted or unsubstituted aryl group having 5 to 15 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 15 ring atoms, or a substituted or unsubstituted non-aromatic group having 5 to 15 ring atoms;
further, Ar1~Ar5Each independently selected from: a substituted or unsubstituted aryl group having 5 to 10 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 10 ring atoms, or a substituted or unsubstituted non-aromatic group having 5 to 10 ring atoms;
further, Ar1~Ar5Each independently selected from: substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl;
further, Ar1~Ar5Each independently selected from: aryl having 5 to 10 ring atoms, heteroaryl having 5 to 10 ring atoms, R1Substituted aryl having 5 to 10 ring atoms, or R1Substituted heteroaryl having 5 to 10 ring atoms;
further, Ar1~Ar5Each independently selected from: phenyl, naphthyl, R1Substituted phenyl or R1Substituted naphthyl;
wherein R is1At each occurrence, the same or different, R1Selected from: H. d, F, Cl, Br, I, CN, NO2、CF3、B(OR2)2,Si(R2)3A linear alkane having 1 to 20 carbon atoms, a branched alkane having 3 to 20 carbon atoms, a cycloalkane having 3 to 20 carbon atoms, an alkane ether having 1 to 20 carbon atoms, an alkane thioether having 1 to 20 carbon atoms, or an alkane ether group having 3 to 20 ring atoms;
R2at each occurrence, the same or different, R2Selected from: H. d, a linear alkyl group having 1 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a silyl group, a substituted keto group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF, a CF group, an isocyano group, an isocyanato group, a hydroxyl group, a cyano group, a haloformyl group, a formyl group, an isocyanato group, a hydroxyl group, a CF group, a C atom, and a3Cl, Br, F, crosslinkable groups, substituted or unsubstituted aryl groups having 5 to 40 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 40 ring atomsSubstituted or unsubstituted heteroaryloxy having 5 to 40 ring atoms, or a combination of these systems; wherein R in one or more radicals2Can form a mono-or polycyclic, aliphatic or aromatic ring system with one another, and/or R in one or more radicals2The rings bonded to the radicals form a mono-or polycyclic, aliphatic or aromatic ring system.
Further, R1At each occurrence, the same or different, R1Selected from: H. d, straight-chain alkyl having 1 to 6C atoms, branched-chain alkyl having 3 to 8C atoms, CF3Cl, Br or F;
further, R1At each occurrence, the same or different, R1Selected from: H. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl or 3, 3-dimethylbutyl or F;
further, R2At each occurrence, the same or different, R2Selected from: a linear alkyl group having 1 to 6C atoms, a branched alkyl group having 3 to 8C atoms, or a cyclic alkyl group having 3 to 8C atoms;
further, the boron-containing compound has a structure represented by formula (II):
wherein, Y1And Y2Each independently is absent or a single bond;
Ar6、Ar7、Ar8and Ar9Each independently is: absent, phenyl or naphthyl;
R21-R24equal to or different from each other, R21-R24At each occurrence, each is independently selected from: H. d, a straight-chain alkyl group having 1 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, an alkoxy group having 1 to 20C atoms, a salt thereof, a stabilizer, a metal,Thioalkoxy having 1 to 20C atoms, silyl, substituted keto groups having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl groups having 7 to 20C atoms, cyano groups, carbamoyl, haloformyl, formyl groups, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF, and the like3Cl, Br, F, a crosslinkable group, a substituted or unsubstituted aryl group having 5 to 40 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 40 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 40 ring atoms, or a combination of these systems;
o is 0, 1,2,3,4, 5 or 6; p is 0, 1,2 or 3; q is 0, 1,2,3,4, 5 or 6;
m is 0, 1,2,3,4 or 5; n is 0, 1,2,3,4 or 5.
In one embodiment, Y1And Y2Are all absent; in one embodiment, Y1And Y2Are all single bonds; in one embodiment, Ar6、Ar7、Ar8And Ar9Are all absent; in one embodiment, Ar6、Ar7、Ar8And Ar9Are all phenyl;
further, R21-R24At each occurrence, each is independently selected from: H. d, straight-chain alkyl having 1 to 8C atoms, branched-chain alkyl having 3 to 8C atoms, alkoxy having 1 to 8C atoms, thioalkoxy having 1 to 8C atoms, cyclic alkyl having 3 to 8C atoms, nitro, CF3Cl, B, F, substituted or unsubstituted aryl having 5 to 10 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 10 ring atoms.
Further, R21-R24At each occurrence, each is independently selected from: H. d, a straight-chain alkyl group having 1 to 6C atoms, a branched-chain alkyl group having 3 to 8C atoms, an alkoxy group having 1 to 6C atoms, a thioalkoxy group having 1 to 6C atoms, a branched-chain alkyl group having 3 to 8C atomsC atom cyclic alkyl, nitro, CF3Cl, B, F, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.
Further, R21-R24At each occurrence, each is independently selected from: H. d, straight-chain alkyl having 1 to 6C atoms, branched-chain alkyl having 3 to 8C atoms, CF3Cl, Br or F.
Further, R21-R24At each occurrence, each is independently selected from: H. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl or 3, 3-dimethylbutyl or F;
further, R21-R24At each occurrence, each is independently selected from: H. isopropyl or F;
further, the boron-containing compound is selected from the compounds of the following structures:
further, the quantum dot material contains at least one material capable of emitting blue light having a peak emission wavelength of 450nm to 460nm, green light having a peak emission wavelength of 520nm to 540nm, red light having a peak emission wavelength of 615nm to 630nm, or a mixture of any two or more thereof. The quantum dots included may be selected from a particular chemical composition, morphology and/or size dimension to achieve light emission at a desired wavelength under electrical stimulation. The narrow particle size distribution of the quantum dots enables the quantum dots to have narrower luminescence spectra. In addition, according to the difference of the adopted chemical composition and structure, the size of the quantum dot needs to be adjusted correspondingly within the size range so as to obtain the luminescent property of the required wavelength.
Further, the luminescent quantum dots are semiconductor nanocrystals. Typically, the semiconductor nanocrystals have a size in the range of about 2 nanometers to about 15 nanometers. In addition, according to the difference of the adopted chemical composition and structure, the size of the quantum dot needs to be adjusted correspondingly within the size range so as to obtain the luminescent property of the required wavelength.
Further, the quantum dot material is selected from: one or more of CdSe, CdS, CdTe, ZnO, ZnSe, ZnS, ZnTe, HgS, HgSe, HgTe, CdZnSe, InAs, InP, InN, GaN, InSb, InAsP, InGaAs, GaAs, GaP, GaSb, AlP, AlN, AlAs, AlSb, CdSeTe and ZnCdSe.
Examples of suitable luminescent quantum dots employing core-shell structures (but not limited to) are:
further, the red light quantum dot material is selected from: CdSe/CdS, CdSe/CdS/ZnS or CdSe/CdSn;
further, the green light quantum dot material is selected from: CdZnSe/CdZnS or CdSe/ZnS;
further, the blue light quantum dot material is selected from: CdS/CdZnS or CdZnS/ZnS.
Further, the mass ratio of the quantum dot material to the boron-containing compound is 1: 0.1-1: 10; further, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 10; further, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 8; furthermore, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 7; furthermore, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 6; furthermore, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 5; furthermore, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 4; furthermore, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 3; furthermore, the mass ratio of the quantum dot material to the boron-containing compound is 1: 1-1: 3; 1: 1-1: 2;
the invention also provides quantum dot ink which comprises the composition and an organic solvent.
Further, in the quantum dot ink, the mass percentage of the composition is 0.2-20%, and the mass percentage of the organic solvent is 80-99.8%.
Further, in the quantum dot ink, the mass percentage of the composition is 0.5-10%, and the mass percentage of the organic solvent is 90-99.5%.
Further, the surface tension of the quantum dot ink at the working temperature or at 25 ℃ is about 19dyne/cm to 50 dyne/cm; further, the surface tension of the quantum dot ink at the working temperature or at 25 ℃ is about 22dyne/cm to 35 dyne/cm; further, the surface tension of the quantum dot ink at the operating temperature or at 25 ℃ is in a range of about 25dyne/cm to 33 dyne/cm.
Further, the viscosity of the above quantum dot ink is in the range of 1cPs to 100cPs at the operating temperature or at 25 ℃. Further, the viscosity of the above quantum dot ink is in the range of 1 to 50cPs at the working temperature or at 25 ℃; further, the viscosity of the above quantum dot ink is in the range of 1.5cPs to 30cPs at the working temperature or at 25 ℃; further, the viscosity of the quantum dot ink is in the range of 4 to 20cPs at the working temperature or at 25 ℃; further, the viscosity of the quantum dot ink is in the range of 4 to 10cPs at the working temperature or at 25 ℃; further, the viscosity of the quantum dot ink is in the range of 5 to 8cPs at the working temperature or at 25 ℃;
it should be noted that the viscosity can also be adjusted by the concentration of the composition in the dot ink, in particular the boron-containing compound in the composition.
Further, the organic solvent in the quantum dot ink is selected from: one or more of an aromatic solvent, a heteroaromatic solvent, an aromatic ketone solvent, an aromatic ether solvent, an aliphatic ketone solvent, an aliphatic ether solvent, an alicyclic solvent, an olefinic solvent, and an inorganic ester solvent.
Further, the aromatic solvent is selected from: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 1, 3-dipropoxybenzene, 4-difluorodiphenylmethane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenylmethane, N-methyldiphenylamine, 4-isopropylbiphenyl, alpha-dichlorodiphenylmethane, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, dibenzyl ether or 2-isopropylnaphthalene;
further, the heteroaromatic solvent is selected from: 2-phenylpyridine, 3-phenylpyridine, 4- (3-phenylpropyl) pyridine, quinoline, isoquinoline, 8-hydroxyquinoline, methyl 2-furancarboxylate or ethyl 2-furancarboxylate;
further, the aromatic ketone solvent is selected from: 1-tetralone, 2-tetralone, acetophenone, propiophenone, or benzophenone, each of said 1-tetralone or 2-tetralone independently optionally substituted with an aliphatic, aryl, heteroaryl, or halogen substituent; each of said acetophenone, propiophenone or benzophenone is independently optionally substituted with methyl;
further, the aromatic ether solvent is selected from: 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethylacetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylbenylether, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran or ethyl-2-naphthyl ether;
further, the ester solvent is selected from: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, or alkyl oleates;
further, the alicyclic solvent is selected from: tetrahydronaphthalene, cyclohexylbenzene, decalin, 2-phenoxytetrahydrofuran, 1' -bicyclohexane, butylcyclohexane, ethyl abietate, benzyl abietate, ethylene glycol carbonate, styrene oxide, isophorone, 3, 5-trimethylcyclohexanone, cycloheptanone, fenchyne, 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, γ -butyrolactone, γ -valerolactone, 6-caprolactone, N-diethylcyclohexylamine, sulfolane or 2, 4-dimethylsulfolane;
further, the aliphatic ketone solvent is selected from: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2, 5-hexanedione, di-n-amyl ketone, phorone, isophorone, 2,6, 8-trimethyl-4-nonanone, camphor or fenchone;
further, the aliphatic ether solvent is selected from: amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether or tetraethylene glycol dimethyl ether;
further, the inorganic ester solvent is selected from: tributyl borate, tripentyl borate, trimethyl phosphate, triethyl phosphate, tributyl phosphate, tris (2-ethylhexyl) phosphate, triphenyl phosphate, diethyl phosphate, dibutyl phosphate, or di (2-ethylhexyl) phosphate.
Further, the quantum dot ink may further include an organic functional material. Organic functional materials include, but are not limited to: any of a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), or the like, or a mixture of any two or more thereof, may be used in the quantum dot ink of the present invention.
The invention also relates to a preparation method of the quantum dot ink, which comprises the following steps: mixing the composition and the organic solvent uniformly; further, the mixing temperature is 40-80 ℃; further, the mixing temperature is 50-70 ℃;
the invention also relates to a functional layer prepared from the quantum dot ink; further, the functional layer is a light emitting layer;
the invention also relates to a preparation method of the functional layer, the quantum dot ink is printed or coated on a preset area by a printing or coating method, wherein the printing or coating method can be selected from (but is not limited to): ink jet Printing, spray Printing (Nozzle Printing), letterpress Printing, screen Printing, dip coating, spin coating, doctor blade coating, roll Printing, twist roll Printing, lithographic Printing, flexographic Printing, rotary Printing, spray coating, brush coating, pad Printing, slot die coating, and the like.
The invention also relates to a quantum dot light-emitting device, which comprises the functional layer, and further comprises but is not limited to: quantum dot light emitting diodes (QLEDs), quantum dot photovoltaic cells (QPV), quantum dot photovoltaic cells (QLEECs), quantum dot field effect tubes (QFETs), quantum dot light field effect tubes, quantum dot lasers, quantum dot sensors, and the like.
Further, as illustrated in fig. 1, the quantum dot light-emitting device includes a light-emitting layer 104, and the light-emitting layer 104 is mainly prepared from the quantum dot ink described above; further, the quantum dot light emitting device further includes an anode 102, a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL)103, an Electron Injection Layer (EIL) or an Electron Transport Layer (ETL)105, and a cathode 10, which are sequentially stacked on the substrate 101.
The present invention will be described below with reference to specific examples.
The boron-containing compounds used in the following examples are shown below;
preparation of quantum dot ink
A stirrer was placed in the vial, and the vial was washed clean and transferred to a glove box. In a vial was prepared 9.5g of dodecylbenzene. And (4) precipitating the quantum dots from the solution by using acetone, and centrifuging to obtain the quantum dot solid. 0.1g of the quantum dot solid and 0.4g of the boron containing compound were weighed into the solvent system in a vial and mixed with stirring in a glove box. Stirring at 60 deg.C until the quantum dots and boron-containing compound are completely dispersed and dissolved, and cooling to room temperature. The resulting solution was filtered through a 0.2um PTFE filter. Sealing and storing.
Wherein, the quantum dot ink 1: comp-1 is matched with blue light quantum dots;
the quantum dot ink 2 is prepared by matching comp-2 with green light quantum dots;
the quantum dot ink is 3: comp-3 matched with red light quantum dots.
Viscosity and surface tension testing
The viscosity of the ink was measured by DV-I Prime Brookfield rheometer; the surface tension of the ink was measured by SITA bubble pressure tensiometer.
Through the test, the viscosity of the ink obtained by the quantum dot ink 1 is 6.2 +/-0.1 cPs, and the surface tension is 29.1 +/-0.1 dyne/cm.
The above tests show that the viscosity of the ink obtained from the quantum dot ink 2 is 6.7 + -0.1 cPs, and the surface tension is 29.5 + -0.1 dyne/cm.
The above tests show that the viscosity of the ink obtained from the quantum dot ink 3 is 7.2 + -0.1 cPs, and the surface tension is 29.6 + -0.1 dyne/cm.
Preparation of quantum dot light-emitting device
The luminescent layer in the quantum dot light-emitting diode is prepared by the quantum dot ink in an ink-jet printing mode, and the method comprises the following specific steps:
the ink was loaded into an ink tank equipped with an inkjet Printer (Dimatix Materials Printer DMP-3000 (Fujifilm)). The waveform, pulse time and voltage of the ejected ink are adjusted to optimize the ink ejection and stabilize the ink ejection range.
The substrate of the device was 0.7mm thick glass sputtered with an Indium Tin Oxide (ITO) electrode pattern. The pixel defining layer is patterned over the ITO to form holes inside for the deposition of printing ink. The HIL/HTL material was then ink-jet printed into the wells and dried at high temperature under vacuum to remove the solvent, resulting in a HIL/HTL film. And then, ink-jet printing the quantum dot ink on the HIL/HTL film, and drying at high temperature in a vacuum environment to remove the solvent to obtain the light-emitting layer film. And then, ink-jet printing the quantum dot ink containing the electron transport performance on the light-emitting layer film, and drying at high temperature in a vacuum environment to remove the solvent to form an Electron Transport Layer (ETL). When an organic electron transport material is used, the ETL may also be formed by vacuum thermal evaporation. Then the Al cathode is formed by vacuum thermal evaporation, and finally the quantum dot light-emitting device is packaged to be prepared.
In summary, the present invention provides a composition comprising a quantum dot material and a boron-containing compound, and a quantum dot light-emitting device prepared by using the ink prepared from the composition has high light-emitting efficiency and long lifetime.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A composition comprising a quantum dot material and a boron-containing compound having a structure according to formula (I);
wherein Ar is1~Ar5At each occurrence, identical or different, Ar1~Ar5Each independently selected from: a substituted or unsubstituted aryl group having 5 to 20 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms, or a substituted or unsubstituted non-aromatic group having 5 to 20 ring atoms;
and Ar is2With said Ar5Connected or not connected, Ar3With said Ar4Connected or not connected.
2. The composition of claim 1, wherein Ar is Ar1~Ar5Each independently selected from: aryl having 5 to 10 ring atoms, heteroaryl having 5 to 10 ring atoms, R1Substituted aryls having 5 to 10 ring atomsRadical, or R1Substituted heteroaryl having 5 to 10 ring atoms;
wherein R is1At each occurrence, the same or different, R1Selected from: H. d, F, Cl, Br, I, CN, NO2、CF3、B(OR2)2,Si(R2)3A linear alkane having 1 to 20 carbon atoms, a branched alkane having 3 to 20 carbon atoms, a cycloalkane having 3 to 20 carbon atoms, an alkane ether having 1 to 20 carbon atoms, an alkane thioether having 1 to 20 carbon atoms, or an alkane ether group having 3 to 20 ring atoms;
R2at each occurrence, the same or different, R2Selected from: H. d, a linear alkyl group having 1 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a silyl group, a keto group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF, an isocyanate group, a hydroxyl group, a cyano group, a formyl group, an isocyanato group, a thiocyanate group, a hydroxyl group, a CF, a3Cl, Br, F, substituted or unsubstituted aryl having 5 to 40 ring atoms, substituted or unsubstituted heteroaryl having 5 to 40 ring atoms, substituted or unsubstituted aryloxy having 5 to 40 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 40 ring atoms, or a combination of these systems; wherein R in one or more radicals2Can form a mono-or polycyclic, aliphatic or aromatic ring system with one another, and/or R in one or more radicals2The rings bonded to the radicals form a mono-or polycyclic, aliphatic or aromatic ring system.
3. The composition of claim 1, wherein the boron-containing compound has a structure represented by formula (II):
wherein, Y1And Y2Each independently is absent or a single bond;
Ar6、Ar7、Ar8and Ar9Each independently is: absent, phenyl or naphthyl;
R21-R24equal to or different from each other, R21-R24At each occurrence, each is independently selected from: H. d, a linear alkyl group having 1 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, an alkoxy group having 1 to 20C atoms, a thioalkoxy group having 1 to 20C atoms, a silyl group, a substituted keto group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF, a CF group, an isocyano group, an isocyanato group, a hydroxyl group, a cyano group, a haloformyl group, a formyl group, an isocyanato group, a hydroxyl group, a CF group, a C atom, and a3Cl, Br, F, a crosslinkable group, a substituted or unsubstituted aryl group having 5 to 40 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 40 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 40 ring atoms, or a combination of these systems;
o is 0, 1,2,3,4, 5 or 6; p is 0, 1,2 or 3; q is 0, 1,2,3,4, 5 or 6;
m is 0, 1,2,3,4 or 5; n is 0, 1,2,3,4 or 5.
4. The composition of claim 3, wherein R is21-R24Equal to or different from each other, R21-R24At each occurrence, each is independently selected from: H. d, straight-chain alkyl having 1 to 6C atoms, branched-chain alkyl having 3 to 8C atoms, CF3Cl, Br or F.
6. the composition of any one of claims 1-5, wherein the quantum dot material is selected from the group consisting of: one or more of CdSe, CdS, CdTe, ZnO, ZnSe, ZnS, ZnTe, HgS, HgSe, HgTe, CdZnSe, InAs, InP, InN, GaN, InSb, InAsP, InGaAs, GaAs, GaP, GaSb, AlP, AlN, AlAs, AlSb, CdSeTe and ZnCdSe.
7. The composition of any one of claims 1-5, wherein the mass ratio of the quantum dot material to the boron-containing compound is 1:0.1 to 1: 10.
8. A quantum dot ink comprising the composition of claims 1-7 and an organic solvent selected from the group consisting of: one or more of an aromatic solvent, a heteroaromatic solvent, an aromatic ketone solvent, an aromatic ether solvent, an aliphatic ketone solvent, an aliphatic ether solvent, an alicyclic solvent, an olefinic solvent, and an inorganic ester solvent.
9. The quantum dot ink as claimed in claim 8, wherein in the quantum dot ink, the mass percentage of the composition is 0.2-20%, and the mass percentage of the organic solvent is 80-99.8%; and/or
The viscosity of the quantum dot ink at 25 ℃ is 1cPs-100 cPs; and/or
The surface tension of the quantum dot ink at 25 ℃ is 19dyne/cm-50 dyne/cn.
10. A quantum dot light emitting device comprising a functional layer prepared mainly from the quantum dot ink according to any one of claims 8 to 9.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011201307.XA CN114031975A (en) | 2020-11-02 | 2020-11-02 | Composition, quantum dot ink and quantum dot light-emitting device |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011201307.XA CN114031975A (en) | 2020-11-02 | 2020-11-02 | Composition, quantum dot ink and quantum dot light-emitting device |
Publications (1)
Publication Number | Publication Date |
---|---|
CN114031975A true CN114031975A (en) | 2022-02-11 |
Family
ID=80134123
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011201307.XA Pending CN114031975A (en) | 2020-11-02 | 2020-11-02 | Composition, quantum dot ink and quantum dot light-emitting device |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114031975A (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018095397A1 (en) * | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | Organic compound containing boron and uses thereof, organic mixture, and organic electronic device |
CN110407859A (en) * | 2019-07-18 | 2019-11-05 | 清华大学 | A kind of luminescent material and its organic electroluminescence device using and comprising it |
JP2020167389A (en) * | 2019-03-29 | 2020-10-08 | 住友化学株式会社 | Light emitting device and manufacturing method thereof, and composition for light emitting element and manufacturing method thereof |
-
2020
- 2020-11-02 CN CN202011201307.XA patent/CN114031975A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018095397A1 (en) * | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | Organic compound containing boron and uses thereof, organic mixture, and organic electronic device |
JP2020167389A (en) * | 2019-03-29 | 2020-10-08 | 住友化学株式会社 | Light emitting device and manufacturing method thereof, and composition for light emitting element and manufacturing method thereof |
CN110407859A (en) * | 2019-07-18 | 2019-11-05 | 清华大学 | A kind of luminescent material and its organic electroluminescence device using and comprising it |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109790407B (en) | Printing ink composition, preparation method and application thereof | |
CN109790406B (en) | Composition for printing electronic device and preparation method and application thereof | |
CN108291105B (en) | Composition for printing electronic devices and use thereof in electronic devices | |
US11512039B2 (en) | Aromatic amine derivatives, preparation methods therefor, and uses thereof | |
US20180346748A1 (en) | Formulation for printing electronic device and application thereof in electronic device | |
CN113698426B (en) | Polycyclic compounds and their use in organic electronic devices | |
WO2017080323A1 (en) | Printing composition and application thereof | |
CN108137971B (en) | Composition for printing electronics and use thereof in electronic devices | |
CN108137972B (en) | Printed electronic composition, electronic device comprising same and preparation method of functional material film | |
US11637257B2 (en) | Electroluminescent material ink and electroluminescent device thereof | |
CN115093333B (en) | Organic compounds, mixtures, compositions and organic electronic devices | |
EP3553152B1 (en) | Mixture, composition and organic electronic device | |
CN111868050A (en) | Composition for preparing organic electronic device, organic electronic device and application | |
WO2022078429A1 (en) | Light-emitting device and use thereof in display | |
CN114195653B (en) | Organic compounds, mixtures, compositions and organic electronic devices | |
CN113816895A (en) | Aromatic amine compound, mixture, composition and organic electronic device | |
CN109790142B (en) | Deuterated aromatic amine derivative and preparation method and application thereof | |
CN114163461B (en) | Fused ring compound containing boron atom and nitrogen atom and application thereof | |
CN114031975A (en) | Composition, quantum dot ink and quantum dot light-emitting device | |
WO2022100099A1 (en) | Compound for organic electroluminescence device | |
CN114075112B (en) | Fluorene compound and application thereof | |
WO2018099433A1 (en) | Fused ring compound and use thereof, mixture and organic electronic device | |
WO2022121224A1 (en) | Organoboron-nitrogen compound, mixture, composition and organic electronic device | |
CN114456158A (en) | Organic compound, mixture, composition and organic electronic device | |
CN114075396A (en) | Composition, printing ink and light-emitting device |
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 | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20220211 |
|
RJ01 | Rejection of invention patent application after publication |