CN111362978B - 一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用 - Google Patents
一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用 Download PDFInfo
- Publication number
- CN111362978B CN111362978B CN201811590545.7A CN201811590545A CN111362978B CN 111362978 B CN111362978 B CN 111362978B CN 201811590545 A CN201811590545 A CN 201811590545A CN 111362978 B CN111362978 B CN 111362978B
- Authority
- CN
- China
- Prior art keywords
- boron
- layer
- light
- blue
- transport layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 61
- -1 Boron-nitrogen heteroaromatic compound Chemical class 0.000 title claims abstract description 29
- 230000005525 hole transport Effects 0.000 claims abstract description 15
- 239000010410 layer Substances 0.000 claims description 65
- 239000002346 layers by function Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 15
- 238000012986 modification Methods 0.000 abstract description 3
- 230000004048 modification Effects 0.000 abstract description 3
- 238000000862 absorption spectrum Methods 0.000 abstract description 2
- 238000000295 emission spectrum Methods 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 description 52
- OCQFHFNWMCLWKC-UHFFFAOYSA-N 1-n,4-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 OCQFHFNWMCLWKC-UHFFFAOYSA-N 0.000 description 14
- WTEJYGDMCOWSLV-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetraphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 WTEJYGDMCOWSLV-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 229910052796 boron Inorganic materials 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 description 4
- 229910052805 deuterium Inorganic materials 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 1
- VPYOROSRDYVFDU-UHFFFAOYSA-N 2,3,5,8-tetraphenylquinoxaline Chemical compound C1=CC=CC=C1C(C1=NC(=C(C=2C=CC=CC=2)N=C11)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 VPYOROSRDYVFDU-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 125000005013 aryl ether group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 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
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005105 dialkylarylsilyl group Chemical group 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 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
- 150000002220 fluorenes Chemical group 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OKPMSRGLGBBULD-UHFFFAOYSA-N n,n-diphenyl-9,9'-spirobi[fluorene]-1-amine Chemical compound C1=CC=CC=C1N(C=1C=2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C=2C=CC=1)C1=CC=CC=C1 OKPMSRGLGBBULD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明属于有机光电材料技术领域，尤其涉及一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用。本发明的化合物通过不同基团的修饰可达到吸收和发射光谱的不同程度的红移，调整杂芳香体系的前线轨道的能量，使其具有较大的Egap，使得其既可与各蓝色客体发光材料搭配构成OLED的发光层，也可以用于OLED器件空穴传输层材料或电子传输层材料；应用于有机电致发光器件中，发光效率高，器件性能得以提升。
Description
技术领域
本发明属于有机光电材料技术领域，尤其涉及一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用。
背景技术
在有机电致发光器件(简称OLED)的研究中，蓝色发光材料是必需的，其本身可以作为发光层制备三基色之一的蓝光OLED，还可以将其他发光材料掺杂在蓝色发光材料中获得绿色和红色的发光器件。蓝色发光材料一般具有宽的能隙，且其电子亲合势(EA)和第一电离能(IP)要匹配。
蓝色发光材料在分子设计上要求材料的化学结构具有一定程度的共轭结构，但分子的偶极不能太大，否则，发光光谱容易红移至绿光区。目前蓝色发光材料主要有只含碳和氢两种元素的芳香型蓝光材料、芳胺类蓝光材料、含硼氮杂环类蓝光材料、有机硅类蓝光材料等。
硼元素，作为元素周期表中碳元素的邻位元素，通常局限性的用于化学试剂和催化剂。含硼有机发光材料总体可以分为两大类，即三价键的硼和四价键的硼。硼元素和氮元素是碳元素临近的两个元素，碳原子和硼原子可以形成稳定的共价键；硼原子最外层电子数为3，而氮原子的最外层电子数为5，因此，硼氮键可以取代芳环中的碳碳键，形成稳定的硼氮杂有机芳香体系，硼氮键在杂芳环中的位置可以调节体系的能带宽度，体系的极性等，因此可能会具有丰富的光电性质。
该类材料不仅可用于OLED器件发光层的主体材料而且还可以用作OLED器件的空穴传输层材料及电子传输层材料。且制备出的OLED器件发光特性好，可用于蓝色等发光器件的制备。
发明内容
本发明针对上述现有技术存在的不足，提供一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用。
本发明解决上述技术问题的技术方案如下：一类用作蓝色荧光材料的硼氮杂芳香化合物，其结构式如下：
X1、X2、X3、X4、X5、X6各自独立的为N或CR1；Y1、Y2各自独立的为N或C；
R1、Ra、Rb各自独立的为氢、氘、卤素、C(＝O)RX、CN、Si(RX)3、P(＝O)(RX)2、ORX、S(＝O)RX、S(＝O)2RX、羰基、N(RX)2、具有1-50个碳原子的烷基或烷氧基、具有3-0个碳原子的环烷基、具有2-50个碳原子的烯基或炔基、具有6-50个芳族环原子的芳族环系或具有5-50个芳族环原子的杂芳族环系中的任意一种；
RX为H、D、F、CN、具有1-50个碳原子的烷基、具有6-50个芳族环原子的芳族环系或具有5-50个芳族环原子的杂芳族环系。
进一步，R1中所述的烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RX基团取代后所得的基团。
进一步，R1中所述的烷基、烷氧基、烯基和炔基包含一个或者多个CH2基团被-RXC＝CRX-、-C≡C-、Si(RX)2、C＝O、C＝N RX、-C(＝O)O-、-C(＝O)N RX-、P(＝O)(RX)、-O-、-S-、SO、或者SO2代替后所得基团。
进一步，RX中所述的烷基、芳族环系和杂芳族环系包含各自被F或CN取代所得的基团。
进一步，任意相邻的两个或多个取代基连接形成环状基团，所述环状基团包含一个以上杂原子，杂原子优选为B、N、S、O或Se。
优选地，上述硼氮杂芳香化合物，具有如下结构式：
本发明的第二个目的在于提供一种硼氮杂芳香化合物的多聚体，由两个以上上述硼氮杂芳香化合物聚合而成。
进一步，硼氮杂芳香化合物彼此之间通过共价键或-(Z)x-的桥基连接；所述Z为B、C、N、O、S、Se、CR2、NR3、AR4R5、具有6-50个芳族环原子的芳族环系、具有5-50个芳族环原子的杂芳族环系、或具有1-50个碳原子的直链或环状的烷基或烷氧基基团；x≥1且为整数，x个Z相互独立；
所述A为C、Si或Ge；
所述R2、R3、R4、R5各自独立的为氢、氘、卤素、C(C＝O)RY、CN、Si(RY)3、P(＝O)(RY)2、ORY、S(＝O)RY、S(＝O)2RY、羰基、N(RY)2、具有6-30个芳族环原子的芳族环系、具有5-30个芳族环原子的杂芳族环系、或具有1-20个碳原子的直链或环状的烷基或烷氧基基团中的任意一种；
RY为H、D、F、CN、具有1-20个碳原子的烷基、具有6-30个芳族环原子的芳族环系或具有5-30个芳族环原子的杂芳族体系。
更进一步，RY中所述的烷基、芳族环系和杂芳族环系包含各自被F或CN取代后所得的基团。
优选地，上述多聚体，具有如下结构式：
本发明的第三个目的在于提供上述硼氮杂芳香化合物或多聚体作为电致发光材料，在有机电致发光器件中的应用。
一种有机电致发光器件，包括阳极层、阴极层和位于阳极层、阴极层之间的功能层，所述功能层中包含上述硼氮杂芳香化合物或多聚体。
进一步，所述功能层是指发光层；所述发光层包括主体发光材料和客体发光材料，上述硼氮杂芳香化合物或多聚体作为主体发光材料。
进一步，所述功能层是指电子传输层或空穴传输层，上述硼氮杂芳香化合物或多聚体作为电子传输层或空穴传输层材料使用。
在本发明上下文中的芳族环系为不包含任何杂原子作为芳族环原子的芳香族环。因此，在本发明上下文中的芳族环系应被理解为体系，不必仅含有芳基基团，而是其中多个芳基基团还可以通过单键或通过非芳香族单元(例如，一个或多个任意选自被取代的C、Si、N、O或S原子)键合。在这种情况下，以体系中非H原子的总数计，所述非芳族单元含有优选小于10％的非H原子。例如，和其中两个或两个以上的芳基基团通过直链或环状的烷基、烯基或炔基基团或通过甲硅烷基基团连接的体系一样，诸如，9，9′-螺二芴、9，9′-二芳基芴、三芳基胺、二芳基醚和茋的体系、取代或未取代的芳氨基、取代或未取代的芳硫基、取代或未取代的芳醚基、取代或未取代的二烷基芳基甲硅烷基、取代或未取代的三芳基甲硅烷基、取代或未取代的芴等等，同样被认为是在本发明上下文中的芳族环系。此外，由2个或2个以上的芳基基团通过单键彼此连接的体系也被认为是在本发明上下文中的芳族环系，例如，诸如联苯和三联苯的体系。
所述杂芳族环系为芳族环原子中至少一个是杂原子的芳香族环。杂原子优选为N、O和/或S。杂芳族环系符合上述芳族环系的定义，但至少一个杂原子作为芳族环原子之一。以这种方式，其不同于在本申请定义的意义上的芳族环系，根据该定义，芳族环系不能含有任何杂原子作为芳族环原子。
芳基基团为含有6-50个芳族环原子，且都不是杂原子。在本发明上下文中的芳基基团被理解为简单的芳族环，即苯或稠合芳族多环，例如萘、蒽或菲。在本申请上下文中的稠合芳族多环由彼此稠合的2个或2个以上简单芳族环组成。环之间稠合在这里被理解为所述环彼此共用至少一个边；
杂芳基基团为含有5-50个芳族环原子，其中至少一个是杂原子。杂芳基基团的杂原子优选为N、O和/或S。在本发明上下文中的杂芳基基团被理解为是指简单的杂芳族环，例如吡啶、嘧啶或噻吩、或稠合杂芳族多环，例如喹啉或咔唑。在本申请上下文中的稠合杂芳族多环由彼此稠合的2个或2个以上简单的杂芳香族环组成。环之间稠合被理解为环彼此共用至少一个边。
具有6-40个芳族环原子的芳族环系或具有5-40个芳族环原子的杂芳族环系，特别被理解为是指衍生自以下的基团：上文在芳基基团下提及的基团，以及联苯、三联苯、四联苯、芴、螺二芴、二氢菲、二氢芘、茚并芴、三聚芴、异三聚芴、螺三聚茚、螺异三聚茚、茚并咔唑，或这些基团的组合。
各自可被上述基团取代并且可经由任何希望的位置与芳族或杂芳族体系连接的芳基或杂芳基基团，特别被理解为是指衍生自如下物质的基团：苯、萘、蒽、菲、芘、二氢芘、
苝、三亚苯、荧蒽、苯丙蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、米并-5，6-喹啉、苯并-6，7-喹啉、苯并-7，8-喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1，2-噻唑、1，3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、喹喔啉、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1，2，3-***、1，2，4-***、苯并***、1，2，3-噁二唑、1，2，4-噁二唑、1，2，5-噁二唑、1，3，4-噁二唑、1，2，3-噻二唑、1，2，4-噻二唑、1，2，5-噻二唑、1，3，4-噻二唑、1，3，5-三嗪、1，2，4-三嗪、1，2，3-三嗪、四唑、1，2，4，5-四嗪、1，2，3，4-四嗪、1，2，3，5-四嗪、嘌呤、喋啶、吲嗪和苯并噻二唑。
在本发明的上下文中具有1-50个碳原子的直链烷基基团、具有3-50个碳原子的支链或环状的烷基基团和具有2～50个碳原子的烯基或炔基基团，优选被理解为是指甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2，2，2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯、环庚烯基、辛烯基、环辛烯基、乙炔基丙炔基、丁炔基、戊炔基、己炔基或辛炔基基团，各个基团中单独的氢原子或者CH2基团也可被上述基团所取代。
本发明的上下文中具有1-50个碳原子的烷基或硫代烷基基团，优选被理解为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基、2，2，2-三氟乙氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、叔丁硫基、仲丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫、五氟乙硫基、2，2，2-三氟乙硫基、乙烯硫基、内烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基，各个基团中单独的氢原子或者CH2基团也可被上述基团所取代。
在本申请的上下文中，2个或2个以上基团一起可形成环的措词应理解为特别是指两个基团通过化学键彼此连接。另外，上述措词也应理解为是指，如果两个基团之一是氢，则第二基团结合于氢原子所键合的位置，从而形成环。
本发明的有益效果是：本发明的化合物通过不同基团的修饰可达到吸收和发射光谱的不同程度的红移，调整杂芳香体系的前线轨道的能量，使其具有较大的Egap，使得其既可与各蓝色客体发光材料搭配构成OLED的发光层，也可以用于OLED器件空穴传输层材料或电子传输层材料；应用于有机电致发光器件中，发光效率高，器件性能得以提升。
附图说明
图1为有机电致发光材料的OLED结构示意图；
图中，1、玻璃衬底；2、阳极层；3、空穴注入层；4、空穴传输层；5、发光层；6、电子传输层；7、电子注入层；8、阴极层。
具体实施方式
以下对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
一、化合物的合成实施例
Ⅰ类化合物T的合成，反应通式如下：
(1)
(2)
(3)
具体制备方法如下：
(1)向经烘箱干燥带有搅拌棒的微波反应瓶中加入R01XBF3K(0.5mmol，1equiv.)，用内衬有一次性聚四氟乙烯薄膜的瓶盖密封该反应瓶，抽真空，氩气清洗三次；氩气保护下，依次加入CPME(0.5mL)和甲苯(0.5mL)、Re1(0.75mmol，1.5equiv.或0.60mmol，1.2equiv.)、SiCl4(0.5mmol，1equiv.)、NEt3(0.75equiv.，如有必要)；得到的混合物在60℃下加热4h或40℃下加热18h后，冷却至室温并用己烷稀释(2mL)；过滤该混合物(2英寸的二氧化硅柱)，并用20％的CH2Cl2/己烷(10ml)淋洗，真空脱溶剂得中间产物INT1a；少数需过柱(30％的CH2Cl2/正己烷作为流动相)；
向带有搅拌棒的圆底烧瓶中加入INT1a，用橡胶垫密封，抽真空，氩气清洗三次，加入无水CH2Cl2(10mL)，冷却至0℃；氩气保护，以1.1mmol/h的速度加入溴的CH2Cl2溶液(352mg，2.2mmol，1.1equiv.)，缓慢升至室温，TLC显示反应结束后，真空脱溶剂；粗产物过柱(0-30％的CH2Cl2/正己烷作为流动相)得中间体INT2a；
(2)无水无氧条件下，将含溴化合物Re2制备成格式试剂INT1b；
(3)向带有搅拌棒的微波反应瓶中依次加入t-Bu3P-Pd-G2(3.3μmol，1mol％)、步骤(1)的反应中间体INT2a(0.33mmol，1equiv.)，用内衬有一次性聚四氟乙烯薄膜的瓶盖密封该反应瓶，抽真空，氩气清洗三次；氩气保护下加入脱气THF(0.8mL)，并降温至0℃；0℃条件下，逐滴加入步骤(2)制备的中间体INT1b(1M的THF溶液，由0.4mL稀释到0.8mL)，用时大于15min；过夜并缓慢升至室温，NH4Cl(0.5mL)的盐溶液淬火，EtOAc(3×2mL)萃取，MgSO4干燥，真空脱溶剂，过柱(硅胶为固定相，0-20％的CH2Cl2/己烷为流动相)，得产物T。
Ⅱ类化合物T1的合成，反应方程式如下：
具体制备方法如下：
向经烘箱干燥带有搅拌棒的微波反应瓶中依次加入R01YBF3K(1.0equiv.)、Re(1.0equiv.)，用内衬有一次性聚四氟乙烯薄膜的瓶盖密封该反应瓶，抽真空，氮气清洗三次后加入CPME(9equiv.)、甲苯(10equiv.)、SiCl4(1.0equiv.)，室温下搅拌2min，氮气保护下加入Et3N(0.75equiv.)，微波辐射下加热至180℃，加热30min后冷却至室温，真空脱溶剂，过柱得T1。
Ⅰ类化合物的合成实施例如表1所示；
表1
Ⅱ类化合物的合成实施例如表2所示；
表2
二、有机电致发光器件应用例
应用例中用到的化合物的结构如下：
应用例1
有机电致发光器件的制备过程如下：
(1)在玻璃底衬1上沉积一层厚度为100nm的氧化铟锡(ITO)作为透明阳极层2；
(2)在透明阳极层2上真空蒸镀厚度为10nm的NPB(N,N’-二(1-萘基)-N,N’-二苯基-1,1’-联苯-4-4’-二胺)空穴传输材料作为空穴注入层3，其中掺杂质量比3％的F4-TCNQ(2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌)；
(3)空穴注入层3上为一层厚度为100nm的spiro-TAD(2,2',7,7'-四(二苯基氨基)-9,9'-螺双芴)作为空穴传输层4；
(4)在空穴传输层4上真空蒸镀一层厚度为30nm的发光层5，发光层包括主体发光材料和客体发光材料；主体发光材料为化合物1，掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)；
(5)再在发光层5上依次真空蒸镀一层厚度为30nm的TPQ(2,3,5,8-四苯基喹喔啉)作为电子传输层6；
(6)在电子传输层6上真空蒸镀厚度为1nm的Liq作为电子注入层7；
(7)最后在电子注入层7上采用真空蒸镀膜沉积技术沉积厚度为100nm的金属铝(Al)作为器件的阴极层8。
应用例2
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物2，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例3
与应用例1相同，与应用例1不同之处在于：电子传输层6为厚度为30nm的化合物3。
应用例4
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物4，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例5
与应用例1相同，与应用例1不同之处在于：电子传输层6为厚度为30nm的化合物5。
应用例6
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物6，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例7
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物7，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例8
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物8，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例9
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物9，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例10
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物10，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例11
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物11，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例12
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度为100nm的化合物12。
应用例13
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度为100nm的化合物13。
应用例14
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物14，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例15
与应用例1相同，与应用例1不同之处在于：电子传输层6为厚度为30nm的化合物15。
应用例16
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物16，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例17
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物17，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例18
与应用例1相同，与应用例1不同之处在于：发光层5为厚度30nm的化合物18，其中掺杂有4wt％的TPPDA(N1，N1，N6，N6-四苯基芘-1，6-二胺)。
应用例1-18的有机电致发光器件性能测试结果如表3、4、5所示；
表3
从表3中的数据可以看出，以本发明提供的材料作为发光层主体材料、TPPDA作为客体发光材料制作的器件，最大电流效率为4.2-5.0cd/A，器件发出的光为蓝色，表明本发明所提供的材料适合于做蓝光主体材料。
表4
从表4中的数据可以看出，以本发明提供的材料作为空穴传输材料制作的器件，最大电流效率为4.4-4.6cd/A，器件发出的光为蓝色，表明本发明所提供的材料适合于做空穴传输材料。
表5
从表5中的数据可以看出，以本发明提供的材料作为电子传输材料制作的器件，最大电流效率为4.4-4.9cd/A，器件发出的光为蓝色，表明本发明所提供的材料适合于做电子传输材料。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。
Claims (4)
1.一类用作蓝色荧光材料的硼氮杂芳香化合物，其特征在于，具有如下结构式：
2.一种有机电致发光器件，包括阳极、阴极和位于阳极、阴极之间的功能层，其特征在于，所述功能层中包含权利要求1所述的用作蓝色荧光材料的硼氮杂芳香化合物。
3.根据权利要求2所述的有机电致发光器件，其特征在于，所述功能层是指发光层，权利要求1所述的用作蓝色荧光材料的硼氮杂芳香化合物在发光层中作为主体发光材料。
4.根据权利要求2所述的有机电致发光器件，其特征在于，所述功能层是指电子传输层或空穴传输层，权利要求1所述的用作蓝色荧光材料的硼氮杂芳香化合物作为电子传输层或空穴传输层材料使用。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811590545.7A CN111362978B (zh) | 2018-12-25 | 2018-12-25 | 一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811590545.7A CN111362978B (zh) | 2018-12-25 | 2018-12-25 | 一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111362978A CN111362978A (zh) | 2020-07-03 |
| CN111362978B true CN111362978B (zh) | 2023-04-07 |
Family
ID=71204032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811590545.7A Active CN111362978B (zh) | 2018-12-25 | 2018-12-25 | 一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111362978B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114874247B (zh) * | 2022-04-28 | 2023-06-16 | 广州追光科技有限公司 | 一种硼氮化合物及包含其的有机电子器件 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1353905A (en) * | 1970-06-10 | 1974-05-22 | Agfa Gevaert | Spectral sensitization of photoconductive compositions |
| CN107353301A (zh) * | 2017-08-28 | 2017-11-17 | 天津理工大学 | 一类硼氮杂芳香化合物及其合成方法及应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10468609B2 (en) * | 2016-06-02 | 2019-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2018
- 2018-12-25 CN CN201811590545.7A patent/CN111362978B/zh active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1353905A (en) * | 1970-06-10 | 1974-05-22 | Agfa Gevaert | Spectral sensitization of photoconductive compositions |
| CN107353301A (zh) * | 2017-08-28 | 2017-11-17 | 天津理工大学 | 一类硼氮杂芳香化合物及其合成方法及应用 |
Non-Patent Citations (3)
| Title |
|---|
| A Convergent, Modular Approach to Functionalized 2,1-Borazaronaphthalenes from 2-Aminostyrenes and Potassium Organotrifluoroborates;Steven R. Wisniewski等;《The Journal of Organic Chemistry》;20131211;第79卷;第368-370页表3-7 * |
| Ladder-Type BN-Embedded Heteroacenes with Blue Emission;Xinyang Wang等;《ORGANIC LETTERS》;20131024;第15卷(第22期);第5715页方案1 * |
| Method for Accessing Nitrogen-Containing, B-Heteroaryl-Substituted 2,1-Borazaronaphthalenes;Geraint H. M. Davies等;《The Journal of Organic Chemistry》;20161214;第82卷;第551页表4化合物7b * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111362978A (zh) | 2020-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN115716838A (zh) | 有机电致发光材料及器件 | |
| JP7274756B2 (ja) | ３つの異なる配位子を含有する金属錯体 | |
| CN113121609B (zh) | 一种金属配合物、包含其的电致发光器件及其用途 | |
| CN115073501A (zh) | 有机电致发光材料及其器件 | |
| CN114605473A (zh) | 一种磷光有机金属配合物及其器件 | |
| CN111349055B (zh) | 一类用作电致发光材料的多环化合物及应用 | |
| CN113968875A (zh) | 一种电致发光材料及器件 | |
| CN114249738B (zh) | 一种电致发光材料及器件 | |
| CN114914372A (zh) | 一种有机电致发光器件 | |
| CN111362978B (zh) | 一类用作蓝色荧光材料的硼氮杂芳香化合物及其应用 | |
| CN111484468B (zh) | 一类用于制备有机光电器件的化合物 | |
| CN113278033B (zh) | 有机电致发光材料及器件 | |
| CN114057797A (zh) | 一种金属配合物、电致发光器件及其应用 | |
| US20230167097A1 (en) | Heterocyclic compound having cyano-substitution | |
| CN113185517A (zh) | 一类用作蓝色荧光材料的氮杂芳香化合物及其应用 | |
| JP2020068383A (ja) | ケイ素含有電子輸送材料およびその使用 | |
| CN114256430B (zh) | 一种电致发光器件 | |
| CN114524850A (zh) | 有机电致发光材料及其器件 | |
| CN108690060B (zh) | 一类用作电致发光材料的多芳香环化合物及其发光装置 | |
| CN114075208A (zh) | 一种电致发光材料及器件 | |
| US20220216433A1 (en) | Electroluminescent device | |
| CN113809242B (zh) | 有机电致发光器件 | |
| US20240032417A1 (en) | Organic electroluminescent material and device thereof | |
| CN111333681B (zh) | 一类用作磷光材料的过渡金属配合物及其应用 | |
| JP2023138428A (ja) | 有機エレクトロルミネッセンス材料およびその素子 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |