CN107667099A - 新颖化合物及包含其的有机发光器件 - Google Patents
新颖化合物及包含其的有机发光器件 Download PDFInfo
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- CN107667099A CN107667099A CN201680033075.7A CN201680033075A CN107667099A CN 107667099 A CN107667099 A CN 107667099A CN 201680033075 A CN201680033075 A CN 201680033075A CN 107667099 A CN107667099 A CN 107667099A
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- Prior art keywords
- alkoxy
- alkyl
- silylation
- halogen
- nitro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 40
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 70
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 150000002367 halogens Chemical class 0.000 claims description 67
- 238000006884 silylation reaction Methods 0.000 claims description 66
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 65
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
- 239000000126 substance Substances 0.000 claims description 59
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000005416 organic matter Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- -1 itrile group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims 2
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 8
- 239000010410 layer Substances 0.000 description 81
- 239000000463 material Substances 0.000 description 55
- 238000000034 method Methods 0.000 description 27
- 230000005540 biological transmission Effects 0.000 description 14
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 11
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 10
- 230000004888 barrier function Effects 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 7
- 230000027756 respiratory electron transport chain Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QFUYDAGNUJWBSM-UHFFFAOYSA-N 1-iodo-2-phenylbenzene Chemical group IC1=CC=CC=C1C1=CC=CC=C1 QFUYDAGNUJWBSM-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 150000002240 furans Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical class BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- DFUGYZQSDFQVPU-UHFFFAOYSA-N 1-benzofuran-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=COC2=C1 DFUGYZQSDFQVPU-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical class C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 1
- KZGFBZWBWJIMDM-UHFFFAOYSA-N 4-N,4-diphenylcyclohexa-1,5-diene-1,4-diamine Chemical class C1(=CC=CC=C1)C1(CC=C(C=C1)N)NC1=CC=CC=C1 KZGFBZWBWJIMDM-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C09B57/008—Triarylamine dyes containing no other chromophores
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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- H10K50/00—Organic light-emitting devices
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Abstract
本发明涉及一种新颖化合物,尤其是涉及形成较深的HOMO的同时具有电子阻隔容易的高LUMO,并具有优秀的空穴迁移率(hole mobility),用作有机发光器件的发光补助层时,抑制滚降(roll off)现象,可实现低电压、高效率、长寿命,并且借助高Tg,驱动有机发光器件时防止重结晶,由此可确保稳定性的新颖化合物。
Description
技术领域
本发明涉及新颖化合物及包含其的有机发光器件,尤其是涉及形成较深的HOMO(最高占据分子轨道)的同时具有电子阻隔容易的高LUMO(最低未占分子轨道),并具有优秀的空穴迁移率(hole mobility),用作有机发光器件的发光补助层时,抑制滚降(roll off)现象,可实现低电压、高效率、长寿命,并且借助高Tg,驱动有机发光器件时防止重结晶,由此可确保稳定性的新颖化合物。
背景技术
最近,能够以自发光型进行低电压驱动的有机发光器件与作为平板显示器件的主流的液晶显示器(LCD,liquid crystal display)相比,视角、对照比等优秀,且不需要背光源,从而可实现轻量化及薄型化,在耗电方面上也有利,且色彩再现范围广,从而作为下一代显示器件备受瞩目。
在有机发光器件中,用作有机物层的材料,按照功能,大体上可分为发光材料、空穴注入材料、空穴传输材料、电子传输材料、电子注入材料等。上述发光材料按照分子量可分为高分子和低分子,按照发光机制可分为来源于电子的单重态激发态的荧光材料和来源于电子的三重态激发态的磷光材料,发光材料按照发光颜色,可分为蓝色、绿色、红色发光材料和为了呈现更好的天然色而所需的黄色及橙色发光材料。并且,为了增加色纯度,并通过能量转移来增加发光效率,可将主体/掺杂剂类用作发光物质。其原理在于,若将与主要构成发光层的主体相比能带隙小且发光效率优秀的少量掺杂剂混合于发光层,则主体中产生的激子向掺杂剂传输,从而发出效率高的光。此时,主体的波长向掺杂剂的波长范围移动,因而根据所利用的掺杂剂和主体的种类可获得所需波长的光。
至今,众所周知,这种有机发光器件中使用的物质有多种化合物,但在利用至今众所周知的物质的有机发光器件的情况下,由于高的驱动电压、低的效率及短寿命,很难进行实用化。因此,利用具有优秀的特性的物质,持续地努力开发具有低电压驱动、高亮度及长寿命的有机发光器件。
并且,最近,对于有机发光器件而言,为了解决空穴传输层中的发光问题,在空穴传输层与发光层之间具有发光补助层。一般来讲,就空穴传输层所使用的物质而言,由于需要具有低HOMO值,因此大部分具有低T1值,由此发光层中生成的激子(exciton)会移到空穴传输层,最终导致发光层内的电荷平衡(charge balance)失去平衡,由此发生在空穴传输层界面上发光的问题。并且,在空穴传输层界面上发光的同时出现色纯度降低及效率减少等问题,而且寿命变短。因此,迫切需要开发出具有高T1值,在空穴传输层HOMO能级与发光层的H OMO能级之间具有HOMO能级的发光补助层中适合用的材料。
发明内容
为了解决如上所述问题,本发明的目的在于,提供形成较深的H OMO的同时具有电子阻隔容易的高LUMO,并具有优秀的空穴迁移率(hole mobility),用作有机发光器件的发光补助层时,抑制滚降(roll off)现象,可实现低电压、高效率、长寿命,并且借助高Tg,驱动有机发光器件时防止重结晶,由此可确保稳定性的新颖化合物。
并且,本发明的目的在于,提供将上述新颖化合物包括在发光补助层,电子阻隔容易,抑制滚降现象,借助低电压、高效率、长寿命及高Tg,驱动时防止重结晶,由此可确保稳定性的有机发光器件。
为了实现上述目的,本发明提供由以下化学式1表示的化合物:
化学式1
在上述化学式1中,
A为以下化学式2,
B为以下化学式3,
Ar为由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
L1、L2分别独立地表示直链;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
及m分别独立地表示0至3的整数,
化学式2
化学式3
在上述化学式2及3中,
*为化学式1中与N相连接的部位,
X为O或S,
Y为O或S,
L3为直链;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及R13分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基,
化学式3的R6、R7、R8、R9中的一个与化学式1的L1或N相连接,
n为0至3的整数。
并且,本发明提供包含由上述化学式1表示的化合物的有机发光器件。
本发明的化合物形成较深的HOMO的同时具有电子阻隔容易的高LUMO,并具有优秀的空穴迁移率(hole mobility),用作有机发光器件的发光补助层时,抑制滚降(roll off)现象,可实现低电压、高效率、长寿命,并且借助高Tg,驱动有机发光器件时防止重结晶,由此可确保稳定性。
附图说明
图1简要示出本发明一实施例的有机发光二极管(OLED)的截面。
附图标记的说明
11:基板 12:阳极
13:空穴注入层 14:空穴传输层
15:发光补助层 16:发光层
17:电子传输层 18:电子注入层
19:阴极
具体实施方式
本发明的化合物,由以下化学式1表示。
化学式1
A为以下化学式2,
B为以下化学式3,
Ar为由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
L1、L2分别独立地表示直链;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
及m分别独立地表示0至3的整数,
化学式2
化学式3
在上述化学式2及3中,
*为化学式1中与N相连接的部位,
X为O或S,
Y为O或S,
L3为直链;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及R13分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基,
化学式3的R6、R7、R8、R9中的一个与化学式1的L1或N相连接,
n为0至3的整数。
具体地,由上述化学式1表示的化合物是由以下化学式4表示的化合物。
化学式4
在上述化学式4中,Ar、X、Y、m及n如化学式1所定义,R14及R15分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基。
更具体地,由上述化学式4表示的化合物是由以下化学式5或6表示的化合物。
化学式5
化学式6
在上述化学式5及6中,X、Y、m及n如化学式1所定义,R14、R15、R16及R17分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基。
具体地,本发明的化合物中,上述之和优选为2以上。这种情况下,适用于有机发光器件时,可更改善寿命及效率。
在本发明中,由上述化学式1表示的化合物的具体例为如下:
本发明的化学式1的化合物形成较深的HOMO的同时具有电子阻隔容易的高LUMO,并具有优秀的空穴迁移率(hole mobility),用作有机发光器件的发光补助层时,抑制滚降(roll off)现象,可实现低电压、高效率、长寿命,并且借助高Tg,驱动有机发光器件时防止重结晶,由此可确保稳定性。尤其是,就化学式5或6而言,可更改善寿命及效率。
并且,本发明的化合物可通过以下反应式1制备而得:
反应式1
在上述反应式中,A、B、Ar、X、Y、L1、L2、L3、m、n、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及R13如化学式1至3所定义。
并且,本发明提供将由上述化学式1表示的化合物包括在有机物层的有机发光器件。具体地,由上述化学式1表示的化合物作为发光补助层包括在有机发光器件。
本发明的有机发光器件包括将由上述化学式1表示的化合物包含在内的1层以上的有机物层,上述有机发光器件的制造方法的一实施例如下。
上述有机发光器件在第一电极(anode)与第二电极(cathod)之间可包括1个以上的空穴注入层(HIL)、空穴传输层(HTL)、发光补助层、发光层(EML)、电子传输层(ETL)、电子注入层(EI L)等有机物层。
首先,在基板11上部蒸镀第一电极用物质来形成第一电极12。此时,上述基板11可使用在常规的有机发光器件中使用的基板,尤其是,使用机械强度、热稳定性、透明性、表面平滑性、处理容易性及防水性优秀的玻璃基板或者透明塑料基板为好。并且,作为第一电极用物质可使用透明而导电性优秀的氧化铟锡(ITO)、氧化铟锌(I ZO)、氧化锡(SnO2)、氧化锌(ZnO)、石墨烯等。上述第一电极用物质可通过常规的阳极形成方法进行蒸镀,具体地可通过蒸镀法或者溅射法进行蒸镀。
其次,可通过真空蒸镀法、旋涂法、浇铸法、LB(Langmuir-Bl odgett)法之类的方法,将空穴注入层13可形成在上述第一电极12上部。
上述空穴注入层物质不受特别限制,具体地可将美国专利第4356429号中揭示的铜酞菁等酞菁化合物或者星爆型胺衍生物类TCTA(4,4',4"-三(N-咔唑基)三苯胺)、m-MTDATA(4,4',4"-三(3-甲苯氨基)三苯胺)、m-MTDAPB(4,4',4"-三(3-甲苯氨基)苯氧基苯)、HI-406(N1,N1'-(联苯-4,4'-二基)双(N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺)等用作空穴注入层物质。
接着,可将空穴传输层14形成在上述空穴注入层13上部。具体地可通过真空蒸镀法、旋涂法、浇铸法、LB法等之类的方法,由空穴传输层物质形成空穴传输层14。
并且,上述空穴传输层物质可从使用于空穴传输层的常规的公知物质中任意选择来使用,具体地,作为公知的上述空穴传输层物质,可使用N-苯基咔唑、聚乙烯基咔唑等咔唑衍生物、N,N'-双(3-甲基苯基)-N,N'-双苯基-[1,1-联苯]-4,4'-二胺(TPD)、N.N'-双(萘-1-基)-N,N'-双苯基联苯胺(α-NPD)等的具有芳香族稠环的常规的胺衍生物等。
并且,在上述空穴传输层14上部形成发光补助层15。上述发光补助层15可通过真空蒸镀法、旋涂法、浇铸法、LB法等之类的方法,可形成发光补助层物质。上述发光补助层物质可使用由本发明的化学式1表示的化合物,还可将公知的发光补助层物质与本发明的由化学式1表示的物质混合来使用。
之后,在上述空穴传输层或有机层(作为一例,发光补助层)上部可形成发光层16。具体地,通过真空蒸镀法、旋涂法、浇铸法、LB法等之类的方法,可形成发光层物质。
并且,上述发光层材料可使用公知的荧光或者磷光的主体或掺杂剂。
此时,作为荧光掺杂剂可使用可从日本出光公司(Idemitsu公司)购买的IDE102或者IDE105,或者BD142(N6,N12-双(3,4-二甲基苯基)-N6,N12-二荚基-6,12-二胺),作为磷光掺杂剂,可共同真空蒸镀(掺杂)绿色磷光掺杂剂Ir(ppy)3(三(2-苯基吡啶)铱)、蓝色磷光掺杂剂F2Irpic(铱(Ⅲ)、双[4,6-二氟苯基)-苯基吡啶-N,C2']吡啶甲酸盐)、UDC公司的红色磷光掺杂剂RD61等。掺杂剂的掺杂浓度不受特别限制。
并且,在发光层16一起使用磷光掺杂剂时,为了防止三重态激子或者空穴扩散到电子传输层17的现象,通过真空蒸镀法或者旋涂法,还可层叠空穴阻挡材料(HBL)。此时可使用的空穴阻挡物质不受特别限制,但可选择任何用作空穴阻挡材料的公知的物质来利用。例如可列举恶二唑衍生物或***衍生物、邻菲咯啉衍生物或日本特开平11-329734(A1)中记载的的空穴阻挡材料等,可使用代表性的Balq(双(8-羟基-2-甲基喹啉)-铝双酚盐)、邻菲咯啉(phenanthrolines)类化合物(例:UDC公司BCP(浴铜灵))等。
在如上所述形成的发光层16上部形成电子传输层17,此时上述电子传输层17可通过真空蒸镀法、旋涂法、浇铸法等方法形成,具体地,可通过真空蒸镀法形成。
上述电子传输层材料起到稳定地传输从电子注入电极注入的电子的功能,其种类不受特别限制,例如可使用喹啉衍生物,尤其可使用三(8-喹啉)铝(Alq3)、或ET4(6,6'-(3,4-二荚基-1,1-二甲基-1H-噻咯-2,5-二基)二-2,2'-联吡啶)。并且,在电子传输层17上部可层叠作为具有从阴极容易注入电子的功能的物质的电子注入层18(EIL),作为电子注入层物质可利用LiF、NaCl、CsF、Li2O、BaO等物质。
并且,可通过真空蒸镀法或溅射等方法,利用第二电极形成用金属,可在电子注入层18上部形成第二电极19。其中,作为第二电极形成用金属可使用金属、合金、导电性化合物及它们的混合物。作为具体例子,有锂(Li)、镁(Mg)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镁-铟(Mg-In)、镁-银(Mg-Ag)、金(Au)、银(Ag)等。并且,为了获得顶部发光器件,还可使用利用ITO、IZO的透过型阴极。
本发明的有机发光器件,不仅可实现第一电极、空穴注入层、空穴传输层、发光补助层、发光层、电子传输层、电子注入层、第二电极结构的有机发光器件,而且还可以实现多种结构的有机发光器件的结构,根据需要,还可形成1层或者2层的中间层。
如上所述,根据本发明形成的各个有机物层的厚度可根据所需的程度进行调节,具体地,可以为5至1,000nm。
并且,在本发明中,包含由上述化学式1表示的化合物的有机物层,由于可按分子单位调节有机物层的厚度,因此具有表面均匀且形态稳定性突出的优点。
本发明的有机发光器件包含具有高LUMO的由上述化学式1表示的化合物,电子阻隔容易,抑制滚降现象,借助低电压、高效率、长寿命及高Tg,驱动时防止重结晶,由此可确保稳定性。
以下,为了有助于理解本发明,提出优选的实施例,但以下实施例仅是用来例示本发明,而本发明的范围并不局限于以下实施例。
中间体IM的合成
在上述式中,L3及n如化学式1所定义。
为了合成目的化合物,IM的准备通过上述步骤进行合成。
IM1的合成
在圆底烧瓶中,将苯并呋喃-3-基-硼酸(benzofuran-3-ylboronic acid)20.0g(初始物质1)、1-溴-4-碘苯(1-bromo-4-iodobenzene)12.6g(初始物质2)溶解于1,4-二恶烷350ml中,并加入K2CO3(2M)100ml和Pd(PPh3)4 2.4g之后进行回流搅拌。用薄层色谱法(TLC)确认反应,并添加水之后结束反应。用MC提取有机层并进行减压过滤之后进行柱纯化,获得13.1g(收率68%)的中间体IM1。
m/z:271.98(100.0%)、273.98(97.3%)、272.99(15.3%)、274.98(14.7%)、273.99(1.3%)、275.99(1.3%)
通过与上述IM1相同的方法,利用不同的初始物质1及初始物质2,合成以下IM2至IM6。(参考以下表1)
表1
中间体IM | 初始物质1 | 初始物质2 |
IM2 | 苯并呋喃-3-基-硼酸 | 4-溴-4'-碘-1,1'-联苯 |
IM3 | 苯并呋喃-3-基-硼酸 | 4'-溴-3-碘-1,1'-联苯 |
IM4 | 苯并[b]噻吩-3-基-硼酸 | 1-溴-4-碘苯 |
IM5 | 苯并[b]噻吩-3-基-硼酸 | 4-溴-4'-碘-1,1'-联苯 |
IM6 | 苯并[b]噻吩-3-基-硼酸 | 4'-溴-3-碘-1,1'-联苯 |
中间体OP的合成
在上述式中,B、L1、L2、Ar、m如化学式1所定义。为了合成目的化合物,OP的准备通过上述步骤进行合成。
OP1的合成
在圆底烧瓶中,将2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]fur an)10g(初始物质1)、[1,1'-联苯基]-4-胺([1,1'-biphenyl]-4-amine)7.5g(初始物质2)、t-BuONa5.8g、Pd2(dba)3 1.5g、(t-Bu)3P1.8ml溶解于甲苯200ml中进行回流搅拌。用薄层色谱法(TLC)确认反应,并添加水之后结束反应。用EA提取有机层并进行减压过滤之后进行柱纯化,获得9.5g(收率70%)的OP1。
m/z:335.13(100.0%)、336.13(26.3%)、337.14(3.5%)
OP7的合成
在圆底烧瓶中,将双(4-溴苯基)胺(bis(4-bromophenyl)ami ne)10.0g(初始物质1)、二苯并[b,d]呋喃-4-基-硼酸(dibenzo[b,d]f uran-4-ylboronic acid)7.2g(初始物质2)溶解于1,4-二恶烷200ml中,并加入K2CO3(2M)50ml和Pd(PPh3)4 1.1g之后进行回流搅拌。用薄层色谱法(TLC)确认反应,并添加水之后结束反应。用M C提取有机层并进行减压过滤之后进行柱纯化,获得10.9g(收率71%)的中间体OP7。
m/z:501.17(100.0%)、502.18(39.3%)、503.18(7.9%)、504.18(1.1%)
通过与上述OP1相同的方法,利用不同的初始物质1及初始物质2,合成以下OP2至OP6,通过与OP7相同的方法,利用不同的初始物质1及初始物质2,合成以下OP8。(参考以下表2)
表2
中间体OP | 初始物质1 | 初始物质2 |
OP2 | 4-溴二苯并[b,d]呋喃 | [1,1'-联苯基]-4-胺 |
OP3 | 2-溴二苯并[b,d]噻吩 | [1,1'-联苯基]-4-胺 |
OP4 | 4-溴二苯并[b,d]噻吩 | [1,1'-联苯基]-4-胺 |
OP5 | 4-(4-溴苯基)二苯并[b,d]呋喃 | [1,1'-联苯基]-4-胺 |
OP6 | 4-(4-溴苯基)二苯并[b,d]噻吩 | [1,1'-联苯基]-4-胺 |
OP8 | 双(4-溴苯基)胺 | 二苯并[b,d]噻吩-4-基-硼酸 |
OP9 | 双(4-溴苯基)胺 | 苯并呋喃-3--基-硼酸 |
OP10 | 双(4-溴苯基)胺 | 苯并[b]噻吩-3-基-硼酸 |
如上述表3所示,本发明的化合物用作发光补助层时,比起比较例1至6,在所有方面上可确认到优秀物性。尤其是,与比较例2至6相比时,即使具有部分相同的苯并呋喃及苯并噻吩,在具有与本发明的化学式1相同的结构的实施例1至24的情况下,形成较深的HOMO的同时在薄膜状态下的分子排列优秀,而且空穴迁移率显著好,由此可知对效率及寿命的提高带来较大影响。
工业实用性
本发明的化合物形成较深的HOMO的同时具有电子阻隔容易的高LUMO,并具有优秀的空穴迁移率(hole mobility),用作有机发光器件的发光补助层时,抑制滚降(roll off)现象,可实现低电压、高效率、长寿命,并且借助高Tg,驱动有机发光器件时防止重结晶,由此可确保稳定性。
Claims (8)
1.一种化合物,其特征在于,由以下化学式1表示:
化学式1
在上述化学式1中,
A为以下化学式2,
B为以下化学式3,
Ar为由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
L1、L2分别独立地表示直链;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
l及m分别独立地表示0至3的整数,
化学式2
化学式3
在上述化学式2及3中,
*为化学式1中与N相连接的部位,
X为O或S,
Y为O或S,
L3为直链;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基、C6-30的芳基、C2-30的杂芳基取代或未取代的C2-50的杂芳基,
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及R13分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基,
化学式3的R6、R7、R8、R9中的一个与化学式1的L1或N相连接,
n为0至3的整数。
2.根据权利要求1所述的化合物,其特征在于,上述化学式1由以下化学式4表示:
化学式4
在上述化学式4中,Ar、X、Y、l、m及n如化学式1所定义,
R14及R15分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基。
3.根据权利要求2所述的化合物,其特征在于,上述化学式4由以下化学式5或6表示:
化学式5
化学式6
在上述化学式5及6中,X、Y、l、m及n如化学式1所定义,R14、R15、R16及R17分别独立地表示氢;重氢;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的烯基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-30的炔基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C1-30的烷氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-30的芳氧基;由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C6-50的芳基;或者由重氢、卤素、氨基、腈基、硝基、C1-20的烷基、C1-20的烷氧基、硅烷基取代或未取代的C2-50的杂芳基。
4.根据权利要求3所述的化合物,其特征在于,上述l+m+n之和为2以上。
5.根据权利要求1所述的有机发光器件,其特征在于,上述化学式1为由以下化学式中的一种表示的化合物:
6.一种有机发光器件,其特征在于,包括:
第一电极,
第二电极,以及
1层以上的有机物层,在两个电极之间含有根据权利要求1所述的化合物。
7.根据权利要求6所述的有机发光器件,其特征在于,上述有机物层为发光补助层。
8.根据权利要求6所述的有机发光器件,其特征在于,上述发光补助层存在于空穴传输层与发光层之间,并与发光层相接。
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