CN104282834B - A kind of composition and its application in organic electronic device - Google Patents
A kind of composition and its application in organic electronic device Download PDFInfo
- Publication number
- CN104282834B CN104282834B CN201410289452.6A CN201410289452A CN104282834B CN 104282834 B CN104282834 B CN 104282834B CN 201410289452 A CN201410289452 A CN 201410289452A CN 104282834 B CN104282834 B CN 104282834B
- Authority
- CN
- China
- Prior art keywords
- organic
- composition
- composition according
- electronic device
- printing
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 78
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims abstract description 26
- YTWOHSWDLJUCRK-UHFFFAOYSA-N thiolane 1,1-dioxide Chemical compound O=S1(=O)CCCC1.O=S1(=O)CCCC1 YTWOHSWDLJUCRK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 238000007639 printing Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 230000004888 barrier function Effects 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 150000003384 small molecules Chemical class 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 5
- 230000005669 field effect Effects 0.000 claims description 4
- 238000013086 organic photovoltaic Methods 0.000 claims description 4
- 239000002861 polymer material Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000008204 material by function Substances 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000005286 illumination Methods 0.000 abstract description 2
- -1 phosphine oxide, sulfoxide Chemical class 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 25
- 239000010410 layer Substances 0.000 description 24
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 20
- 239000003446 ligand Substances 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 150000004982 aromatic amines Chemical class 0.000 description 11
- 150000004696 coordination complex Chemical class 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 10
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 229930192474 thiophene Natural products 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 150000001339 alkali metal compounds Chemical class 0.000 description 9
- 239000003205 fragrance Substances 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 150000002220 fluorenes Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 7
- 229960005544 indolocarbazole Drugs 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 150000001345 alkine derivatives Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229910052762 osmium Inorganic materials 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- KAZPHAGSWZTKDW-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-amine Chemical compound COC1=CC=C(CC(C)N)C=C1OC KAZPHAGSWZTKDW-UHFFFAOYSA-N 0.000 description 4
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 4-amino-o-xylene Natural products CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 4
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 4
- 239000013110 organic ligand Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 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
- 229920000642 polymer Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 238000007650 screen-printing Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 3
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 3
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 3
- OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 3
- QZLAKPGRUFFNRD-UHFFFAOYSA-N [1]benzoselenolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3[se]C2=C1 QZLAKPGRUFFNRD-UHFFFAOYSA-N 0.000 description 3
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 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 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 3
- 150000002240 furans Chemical class 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 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 3
- 150000002475 indoles Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 3
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 3
- 150000004893 oxazines Chemical class 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 150000004867 thiadiazoles Chemical class 0.000 description 3
- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- KIDLUFAKISHFQQ-UHFFFAOYSA-N 2-phenylpyridine Chemical class C1(=CC=CC=C1)C1=NC=CC=C1.C1(=CC=CC=C1)C1=NC=CC=C1 KIDLUFAKISHFQQ-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical class C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 2
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229910052768 actinide Inorganic materials 0.000 description 2
- 150000001255 actinides Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002322 conducting polymer Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- CUIWZLHUNCCYBL-UHFFFAOYSA-N decacyclene Chemical compound C12=C([C]34)C=CC=C4C=CC=C3C2=C2C(=C34)C=C[CH]C4=CC=CC3=C2C2=C1C1=CC=CC3=CC=CC2=C31 CUIWZLHUNCCYBL-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- SWGQKRKXZZPKJA-UHFFFAOYSA-N indeno[2,1-a]fluorene-1,2-diamine Chemical class C1=CC=C2C=C3C4=CC5=C(N)C(N)=CC=C5C4=CC=C3C2=C1 SWGQKRKXZZPKJA-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000001755 magnetron sputter deposition Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000000434 metal complex dye Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 238000010020 roller printing Methods 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical class ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical compound C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 description 1
- NVUJWPQINQUNNM-UHFFFAOYSA-N 1h-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1.C1=CC=C2NC=NC2=C1 NVUJWPQINQUNNM-UHFFFAOYSA-N 0.000 description 1
- HIISVQYDQWJITQ-UHFFFAOYSA-N 1h-pyrrole;quinoline Chemical class C=1C=CNC=1.N1=CC=CC2=CC=CC=C21 HIISVQYDQWJITQ-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 description 1
- LVUBSVWMOWKPDJ-UHFFFAOYSA-N 4-methoxy-1,2-dimethylbenzene Chemical compound COC1=CC=C(C)C(C)=C1 LVUBSVWMOWKPDJ-UHFFFAOYSA-N 0.000 description 1
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- 235000000621 Bidens tripartita Nutrition 0.000 description 1
- 240000004082 Bidens tripartita Species 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- SKLCPEMSKRYVKF-UHFFFAOYSA-N C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1.C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1.C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 SKLCPEMSKRYVKF-UHFFFAOYSA-N 0.000 description 1
- UWWFPDZLJWNMJU-UHFFFAOYSA-N C1=CC=CC2=CC=C3C(=C12)CC=1C=CC=CC13.C1=C3C=C2C(=CC=C4C=5C=CC=CC5C=C24)C3=CC=C1 Chemical compound C1=CC=CC2=CC=C3C(=C12)CC=1C=CC=CC13.C1=C3C=C2C(=CC=C4C=5C=CC=CC5C=C24)C3=CC=C1 UWWFPDZLJWNMJU-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004890 Hydrophobing Agent Substances 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 229910015711 MoOx Inorganic materials 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical class C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005606 carbostyryl group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- SIFHTIHFPPIGBL-UHFFFAOYSA-N ctk2i0750 Chemical compound C12=C3C4=CC=CC3=CC=C2C=CC=C1C1=C4CC2=CC=CC=C21 SIFHTIHFPPIGBL-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 208000006637 fused teeth Diseases 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-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
- 150000007530 organic bases Chemical class 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000005063 oxadiazines Chemical class 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- YHFIVLSFOFRCGW-UHFFFAOYSA-N perylene pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 YHFIVLSFOFRCGW-UHFFFAOYSA-N 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
- 150000002991 phenoxazines Chemical class 0.000 description 1
- STKKCWNZZPGJHR-UHFFFAOYSA-N phosphane;styrene Chemical compound P.C=CC1=CC=CC=C1 STKKCWNZZPGJHR-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 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
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a kind of novel compositions, it include sulfolane (Sulfolane) or dimethyl sulfone (Dimethyl sulfone), at least one organic functional material, and a kind of organic solvent, and its in organic electronic device, the production method of application and organic electronic device in special luminescent device and its application in illumination and display technology and other occasions.
Description
Technical field:
The present invention relates to a kind of novel compositions, include sulfolane (Sulfolane) or dimethyl sulfone (Dimethyl
Sulfone) and at least one organic functional material, and its application in organic electronic device, special luminescent device, and
The production method of organic electronic device and its application in illumination and display technology and other occasions.
Background technique:
Organic luminescent device, especially Organic Light Emitting Diode (OLED) are (referring to TANG etc.
Appl.Phys.Lett.1987,51, p913), since it is from main light emission, high brightness, it is abundant by chemical synthesis to color
Adjustability, flexibility etc. become next-generation display most promising at present and lighting engineering.Especially they may pass through printing
Method, such as inkjet printing (InkJet Printing), the technologies such as silk-screen printing (Screen Printing) form a film from solution,
So as to substantially reduce manufacturing cost, therefore to large screen display and luminaire with regard to particularly attractive.
OLED based on small molecule is had excellent performance, and has reached the commercialized stage, but it can only pass through the vacuum evaporation side of obtaining
Method preparation.The solution viscosity of small molecule material is too low, so that it is difficult to form a film from solution by the method for printing.Chinese patent
CN102668152 is using neutral high polymer material as the composition containing Small molecule organic materials of additive for application, and takes
The Ink Jet Printing Performance that must be got well.But neutral additive often damages the performance of organic electronic device.
Summary of the invention
The shortcomings that in order to overcome existing membrane electro luminescent device in summary, the present invention provide a kind of novel group
Object is closed, includes sulfolane (Sulfolane) or dimethyl sulfone (Dimethyl sulfone), especially sulfolane, and at least
A kind of organic functional material, thus the technology choosing for extending the coating that can be used for preparing organic electronic device or printing ink
?.Composition according to the invention has adjustable viscosity, to be suitable for the method for different printing or printing.The present invention
Second purpose be to provide this composition as coating or printing ink in the purposes for preparing organic electronic device.Of the invention
Third purpose is to provide a kind of organic electronic device, includes one or more layers organic functional thin film, wherein at least there is one layer
Film is prepared from composition according to the invention, is prepared especially by the method for printing or printing.
The detailed description of invention
It should be appreciated that the specific implementation of the description and display done below is example of the invention, be not meant to
In addition any mode limits the scope of the invention.In fact, for purposes of brevity, conventional electricity may be not described in herein
Other functions of sub- device, manufacturing method, semiconductor devices and relevant organic material and system.
The present invention provides a kind of novel composition, and it includes have sulfolane (Sulfolane) or dimethyl sulfone
(Dimethyl sulfone) and one or more organic functional materials, it is characterised in that at least a kind of organic functional material
It is small molecule material.
In a preferential embodiment, the composition includes sulfolane (Sulfolane).
In the present invention, Small molecule organic materials refer to that molecular weight is at most the material of 5000g/mol, and molecular weight is higher than
The material of 5000g/mol is referred to as high polymer.In a preferential embodiment, the composition includes one or more
Small organic molecule functional material.
In the present invention, organic functional material refers to the organic material with an electronics or optical property, and hole is (also referred to as electric
Hole) injection or transmission material (HIM/HTM), hole barrier materials (HBM), electron injection or transmission material (EIM/ETM), electronics
Barrier material (EBM), organic host materials (Host), singlet emitters (fluorescent illuminant), (phosphorescence shines weight state illuminator
Body), especially luminescent organometallic complex compound and dyestuff.In the present invention, Host, material of main part, basis material and matrix material
Material has the same meaning, they can be interchanged.Suitable organic functional material is being discussed in detail herein below.It is now right
Some preferential embodiments are made an explanation.
In a preferential embodiment, the composition, one or more of them organic functional material is selected from sky
Hole injection material (HIM) hole mobile material (HTM) or electron-blocking materials (EBM) or their various combinations.
Preferential organic HTM or HIM or EBM material be optional include following structural unit compound: phthalocyanine
(phthlocyanine), porphyrin (porphyrine), amine (amine), aromatic amine, biphenyl class triaryl amine (triarylamine),
Thiophene (thiophene), bithiophene (fused thiophene) is such as dithienothiophene (dithienothiophene) and simultaneously
Thiophene (dibenzothiphene), pyrroles (pyrrole), aniline (aniline), carbazole (carbazole), indolocarbazole
(indolocarbazole), and their derivative.
In another preferential embodiment, the composition, one or more of them organic functional material is selected from
Electron injection material (EIM) electron transport material (ETM) or hole barrier materials (HBM) or their various groups
It closes.Preferred ETM or EIM or HBM material are aromatic ketone, aromatics phosphine oxide, sulfoxide, aromatics, aromatic sulfones, the gold of pyrrolotriazine derivatives
Belong to the complex of complex compound, especially aluminum and zinc, anthracene derivant, benzimidizole derivatives etc..
In an especially preferential embodiment, the composition includes that an organic luminorphor and one have owner
Body material.Its organic luminorphor can be selected from fluorescent illuminant (also referred to as singlet emitters (Singlet Emitter)) or phosphorescence
Illuminator (also referred to as triplet emitters (Triplet Emitter)).In general, in the luminescent layer of luminescent device (EML),
Material of main part is the component to occupy the majority.
In another preferential embodiment, the composition in the present invention includes an organic singlet emitters
(Singlet Emitter) and organic singlet state host material (Singlet Host).Singlet emitters are in luminescent layer
Ratio be 1-25wt%, preferably 2-20wt%, more preferably 3-15wt%, preferably 5-10wt%.Organic singlet luminescent
The example of body and organic singlet state host material will be described below.
In another preferential embodiment, the composition in the present invention includes a triplet emitters (Triplet
) and an organic triplet host material (Triplet Host) Emitter.Ratio of the triplet emitters in luminescent layer is 1-
25wt%, preferably 5-25wt%, more preferably 5-20wt%, preferably 10-20wt%.Triplet emitters and organic triplet
The example of host material will be described below.
Preferably the example of singlet emitters is
The example of preferred triplet emitters has
In certain embodiments, the composition also includes high polymer material.All includes small point as described herein
The structure of sub- material is all suitable material as the high polymer material of repetitive unit.In a preferential embodiment, this
Composition in invention includes conjugated highpolymer, and suitable conjugated highpolymer has polyfluorene (polyfluorene), poly- spiral shell-difluorene
(poly (spiro-bifluorene)), poly- indenofluorene (polyindenofluorene) are poly- (p-phenylene-ethenylidene)
(poly (p-phenylen-vinylene)), poly- (to phenylene) (poly (para-phenylene)), extremely derivative.
In a preferential embodiment, the composition includes at least another organic solvent.Organic solvent
Example, including but not limited to, methanol, ethyl alcohol, 2-methyl cellosolve, methylene chloride, chloroform, chlorobenzene, o-dichlorohenzene,
Tetrahydrofuran, methyl phenyl ethers anisole, morpholine, toluene, ortho-xylene, meta-xylene, paraxylene, Isosorbide-5-Nitrae dioxane, acetone, first
Base ethyl ketone, 1,2 dichloroethanes, 3- phenoxytoluene, 1,1,1- trichloroethanes, 1,1,2,2- tetrachloroethanes, ethyl acetate, vinegar
Acid butyl ester, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide, naphthane, naphthalane, indenes and/or their mixture.
In certain embodiments, by adjusting the ratio of sulfolane (Sulfolane) or dimethyl sulfone and organic solvent, institute
Viscosity when stating 25 DEG C of composition is within the scope of 1.5 to 40mPs, the method for making it suitable for different printing or printing, preferentially
Within the scope of 2.5 to 30mPs, more preferably within the scope of 2.5 to 20mPs.In certain embodiments, sulfolane
(Sulfolane) or the weight rate of dimethyl sulfone and organic solvent be from 10:90 to 90:10, preferably from 20:80 to
80:20, preferably from 30:70 to 70:30.
In a preferential embodiment, composition according to the invention is a solution.
In another embodiment, composition according to the invention is a suspension.
Composition of the invention can include 0.01 to 20wt%, preferably 0.1 to 15wt%, more preferable 0.2 to 10wt%,
Most preferably 0.25 to 5wt% organic functional material.The percent data is related to 100% solvent or solvent mixture and ring
Fourth sulfone or dimethyl sulfone.
Purposes the invention further relates to the composition as coating or printing ink when preparing organic electronic device, it is special
Not preferential is the preparation method by printing or being coated with.
Suitable printing or coating technique includes but is not limited to inkjet printing, typographic printing, silk-screen printing, dip-coating, rotation
Turn to be coated with, blade coating, roller printing, torsion roller printing, lithographic printing, flexographic printing, rotary printing, spraying is brushed or moved
Print, slit-type squash type coating etc..It is preferred that intaglio printing, silk-screen printing and ink jet printing.Intaglio printing, ink jet printing will
It applies in an embodiment of the present invention.Solution or suspension can also comprise one or more components such as surface-active chemical combination
Object, lubricant, wetting agent, dispersing agent, hydrophobing agent, bonding agent etc., for adjusting viscosity, filming performance improves adhesion etc..Have
Close printing technique, and its to the related request in relation to solution, such as solvent and concentration, viscosity etc., details refer to
Helmut Kipphan chief editor " print media handbook: technology and production method " (Handbook of Print Media:
Technologies and Production Methods),ISBN3-540-67326-1。
It include one or more layers organic functional thin film, wherein at least the invention further relates to an organic electronic device
Thin film is prepared by composition according to the invention, is prepared especially by the method for printing or coating.
Suitable organic electronic device includes but is not limited to Organic Light Emitting Diode, organic light emission battery, organic photovoltaic electricity
Pond, organic field-effect tube, organic light-emitting field effect pipe, organic sensor.Preferred organic electronic device has organic light-emitting diodes
Pipe, organic photovoltaic battery.
In above-described luminescent device, including a substrate, an anode, at least a luminescent layer, a cathode.Substrate can be
It is opaque or transparent.One transparent substrate can be used to manufacture a transparent light emitting component.It see, for example,
The Nature1996 such as Bulovic, 380, p29 and Gu etc., Appl.Phys.Lett.1996,68, p2606.Substrate can be just
It is property or elastic.Substrate can be plastics, metal, semiconductor wafer or glass.Preferably substrate has a smooth surface.
Substrate free of surface defects is especially desirable selection.In a preferential embodiment, substrate it is optional in thin polymer film or
Plastics, glass transition temperature Tg is 150 DEG C or more, preferably more than 200 DEG C, more preferably more than 250 DEG C, preferably more than 300
℃.The example of suitable substrate has poly- (ethylene glycol terephthalate) (PET) and polyethylene glycol (2,6- naphthalene) (PEN).
Anode may include a conductive metal or metal oxide or conducting polymer.Anode can be easily injected into hole
Into HIL or HTL or luminescent layer.In one embodiment, inorganic semiconductor illuminator in the work function and luminescent layer of anode
Or the HOMO energy level of the p-type semiconductor material as HIL or HTL or EBL or the absolute value of the difference of valence-band level are less than 0.5eV,
Preferably it is less than 0.3eV, preferably less than 0.2eV.The example of anode material includes but is not limited to Al, Cu, Au, Ag, Mg, Fe,
Co, Ni, Mn, Pd, Pt, ITO, aluminium-doped zinc oxide (AZO) etc..Other suitable anode materials be it is known, this field is common
Technical staff is readily able to select use.Any suitable technology deposition, such as a suitable physics gas can be used in anode material
Phase sedimentation, including rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc..
In certain embodiments, anode is patterning.Patterned ITO electrically-conductive backing plate is commercially available,
And it can be used to prepare device according to the present invention.
Cathode may include a conductive metal or metal oxide.Cathode can be easily injected into electronics to EIL or ETL or straight
It is connected in luminescent layer.In one embodiment, inorganic semiconductor illuminator or as EIL in the work function and luminescent layer of cathode
Or the lumo energy of the n-type semiconductor of ETL or HBL or the absolute value of the difference of conduction level are less than 0.5eV, are preferably less than
0.3eV, preferably less than 0.2eV.In principle, the material of all cathodes that can be used as OLED all may be as device of the present invention
Cathode material.The example of cathode material includes but is not limited to Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/
Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO etc..Any suitable technology deposition, such as a suitable object can be used in cathode material
Physical vapor deposition method, including rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc..
In a preferential embodiment, in luminescent device according to the invention, luminescent layer is by the printing present invention
Composition be prepared.
The invention further relates to the application of luminescent device according to the invention in electronic equipment of various, include, but are not limited to
Show equipment, lighting apparatus, light source, sensor etc..
The invention further relates to the electronic equipments for including luminescent device according to the invention, include, but are not limited to display and set
It is standby, lighting apparatus, light source, sensor etc..
Some more detailed descriptions (but not limited to this) are made to organic functional material below.In principle, all to be used for
The organic functional material of OLEDs, including hole (also referred to as electric hole) injection or transmission material (HIM/HTM), hole barrier materials
(HBM), electron injection or transmission material (EIM/ETM), electron-blocking materials (EBM), organic host materials (Host), singlet state
Illuminator (fluorescent illuminant), weight state illuminator (phosphorescent emitter), especially luminescent organometallic complex compound, can be used in this
In the luminescent device of invention.Such as to various in WO2010135519A1, US20090134784A1 and WO2011110277A1
Organic functional material is described later in detail, and is hereby incorporated herein by reference the full content in this 3 patent document.
1.HIM/HTM
Suitable organic HTM material is optional include following structural unit compound: phthalocyanine (phthlocyanine),
Porphyrin (porphyrine), amine (amine), aromatic amine, biphenyl class triaryl amine (triarylamine), thiophene (thiophene),
Bithiophene (fused thiophene) such as dithienothiophene (dithienothiophene) and bithiophene
(dibenzothiphene), pyrroles (pyrrole), aniline (aniline), carbazole (carbazole), indolocarbazole
(indolocarbazole), and their derivative.The suitable HTM of another position also includes containing fluorohydrocarbon
(fluorohydrocarbon) polymer；Polymer containing conductiving doping；Conducting polymer, such as PEDOT/PSS；From group
Fill monomer, such as compound containing phosphonic acids and sliane derivative；Metal oxide, such as MoOx；Metal complex and Cross-linked
Close object etc..
The example that can be used as the cyclophane perfume (or spice) amine derivative compounds of HIM or HTM includes but is not limited to following general structure:
Each Ar1To Ar9It can be independently selected from aromatic hydrocarbon ring compound, such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene,
Phenalene, luxuriant and rich with fragrance, fluorenes, pyrene are bent, Azulene；Heteroaromatic compound, such as dibenzothiophenes, dibenzofurans, furans, thiophene,
Benzofuran, benzothiophene, carbazole, pyrazoles, imidazoles, triazole, isoxazole, thiazole, oxadiazoles, oxatriazole, two dislike
Azoles, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, oxathiazine, oxadiazine, indoles, benzimidazole,
Indazole, indoxazine, benzoxazoles, benzisoxazole, benzothiazole, quinoline, isoquinolin, cinnoline, quinoline azoles
Quinoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, phenthazine, phenoxazine, dibenzoselenophene,
Benzoselenophene, benzofuropyridine, indolocarbazole, pyridylindole,
Pyrrolodipyridine, furodipyridine, benzothienopyridine, thienodipyridine,
Benzoselenophenopyridine and selenophenodipyridine；It include the group of 2 to 10 ring structures, they
It can be the aromatic hydrocarbon ring group or aromatic heterocycle group of identical or different type, and directly with one another or by below at least one
Group link together, such as oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structural unit and fat
Cyclic group.Wherein, each Ar can be further substituted, and substituent group is chosen as hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl
Base, miscellaneous alkyl, aryl and heteroaryl.
In one aspect, Ar1To Ar9It can be independently selected from comprising the group such as the following group:
Wherein, n is 1 to 20 integer；X1To X8It is CH or N；Ar1It is aryl or heteroaryl.
The other example of cyclophane perfume (or spice) amine derivative compounds can be found in US3567450, US4720432, US5061569,
US3615404, and US5061569.
The example that can be used as the metal complex of HTM or HIM includes but is not limited to following general structure:
M is a metal, there is the atomic weight greater than 40；
(Y1-Y2) it is one liang of tooth ligand, Y1And Y2Independently selected from C, N, O, P, and S；L is an assistant ligand；M is one
Integer, value from 1 to this metal maximum coordination number；M+n is the maximum coordination number of this metal.
In one embodiment, (Y1-Y2) it is a 2- phenylpyridine derivative
In another embodiment, (Y1-Y2) it is a carbenes
In another embodiment, M choosing is in Ir, Pt, Os, and Zn.
On the other hand, the HOMO of metal complex is greater than -5.5eV (relative to vacuum level)
The example that suitably can be used as HIM/HTM compound is listed in following table:
2.EIM/ETM
In principle, suitable N-shaped organic semiconducting materials are optional in all EIM/ETM for OLEDs.EIM/ETM
The example of material is not particularly limited, and any metal complex or organic compound may all be used as ETM, as long as it
Can transmit electronics.Preferential organic ETM material can be selected from three (8-hydroxyquinoline) aluminium (AlQ3), azophenlyene (Phenazine),
Phenanthroline (Phenanthroline), anthracene (Anthracene), luxuriant and rich with fragrance (Phenanthrene), fluorenes (Fluorene), two fluorenes
(Bifluorene), two fluorenes of spiral shell (Spiro-bifluorene), to phenylacetylene (Phenylene-vinylene), triazine
(triazine), triazole (triazole), imidazoles (imidazole), pyrene (Pyrene), (Perylene), anti-indenofluorene
(trans-Indenofluorene), along indeno (cis-Indenonfluorene), dibenzo-indenofluorene (Dibenzol-
), indenofluorene indeno naphthalene (Indenonaphthalene), benzanthracene (benzanthracene) and their derivative
Object
On the other hand, the compound that can be used as EIM/ETM is the molecule for containing at least one following group:
R1It is optional in following group: hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl and heteroaryl
Base, the Ar when they are aryl or heteroaryl, in they and above-mentioned HTM1And Ar2Meaning is identical；
Ar1-Ar5With the Ar described in HTM1Meaning is identical；
N is an integer from 0 to 20；
X1-X8It selects in CH or N.
On the other hand, the example that can be used as the metal complex of EIM/ETM includes but is not limited to following general structure:
(O-N) or (N-N) is one liang of tooth ligand, wherein metal and O, N or N, N coordination；L is an assistant ligand；M is one
Integer, value from 1 to this metal maximum coordination number.
In another preferential embodiment, organic alkali metal compound can be used as EIM.In the present invention, organic base
It is following compound that metallic compound, which is understood that dig, and wherein at least one alkali metal, i.e. lithium, sodium, potassium, rubidium, caesium goes forward side by side
One step includes at least one organic ligand.
In suitable organic alkali metal compound, including US 7767317B2, EP 1941562B1 and EP 1144543B1
Described compound.
The organic alkali metal compound preferentially selected is the compound of following chemical formula:
Wherein R1Meaning as described above, camber line represents two or three atoms and bonded, so as to when necessary with metal M
5 yuan or hexatomic ring are formed, wherein atom can also be by one or more R1Replace, M is alkali metal, be selected from lithium, sodium, potassium, rubidium,
Caesium.
Organic alkali metal compound can have the form of monomer, as described above, or have the form of aggregation, for example,
Two alkali metal ions and two ligands, 4 alkali metal ions and 4 ligands, 6 alkali metal ions and 6 ligands or in other forms.
The organic alkali metal compound especially preferentially selected is the compound of following chemical formula:
Symbol used in it has above-mentioned definition identical, in addition:
O, can be identical or different when occurring every time, be 0,1,2,3 or 4；
P, can be identical or different when occurring every time, be 0,1,2 or 3；
In a preferential embodiment, alkali metal M is selected from lithium, sodium, potassium, more preferably lithium or sodium, preferably lithium.
In a preferential embodiment, in organic alkali metal compound electron injecting layer preferably, electron injecting layer
It is made of organic alkali metal compound.
In another preferential embodiment, organic alkali metal compound is doped in other ETM and forms electron-transport
Is electron transfer layer preferably in layer or electron injecting layer.
The example of suitable organic alkali metal compound is listed in following table:
3. triplet host material (Triplet Host):
The example of triplet host material is not particularly limited, and any metal complex or organic compound all may
It is used as matrix, as long as its triplet energy ratio illuminator, especially triplet emitters or phosphorescent emitter are higher.
The example that can be used as the metal complex of triplet matrix (Host) includes but is not limited to following general structure:
M is a metal；(Y3-Y4) it is one liang of tooth ligand, Y3And Y4Independently selected from C, N, O, P, and S；L is an auxiliary
Ligand；M is an integer, value from 1 to this metal maximum coordination number；M+n is the maximum coordination number of this metal.
In a preferential embodiment, the metal complex that can be used as triplet matrix has following form:
It (O-N) is one liang of tooth ligand, wherein metal and O and N Atomic coordinate
In some embodiment, M is optional in Ir and Pt.
Can be used as the organic compound of triplet matrix example be selected from include aromatic hydrocarbon ring base compound, hinder as
Benzene, biphenyl, triphenyl, benzo, fluorenes；Test；It include the compound of fragrant heterocyclic radical, such as dibenzothiophenes, dibenzofurans,
Dibenzoselenophene, furans, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole,
Indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazoles, imidazoles, triazole type, oxazole, thiazole are disliked
Diazole, oxatriazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazines, oxazines,
Oxathiazines, oxadiazines, indoles, benzimidazole, indazole, indoxazine, bisbenzoxazoles,
Benzisoxazole, benzothiazole, quinoline, isoquinolin, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene,
Acridine, azophenlyene, phenthazine, phenoxazines, benzofuropyridine, furodipyridine,
Benzothienopyridine, thienodipyridine, benzoselenophenopyridine and
selenophenodipyridine；It include the group of 2 to 10 ring structures, they can be the cyclophane of identical or different type
Fragrant hydrocarbyl group or aromatic heterocycle group, and link together directly with one another or by least one group below, such as oxygen atom,
Nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structural unit and aliphatic cyclic group.Wherein, each Ar can be into one
Step is substituted, and substituent group is chosen as hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl and heteroaryl.
In a preferential embodiment, triplet host material is optional in the compound comprising at least one following group:
Ar1-Ar3With the Ar described in HTM1Meaning is identical, R1-R7It can select independently of each other in following group: hydrogen,
Alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl and heteroaryl, when they are aryl or heteroaryl
When base, Ar described in they and above-mentioned HTM1And Ar2Meaning is identical；
N is an integer from 0 to 20；X1-X8It selects in CH or N；X9It selects in CR1R2Or NR1。
4. singlet state host material (Singlet Host):
The example of singlet state host material is not particularly limited, and any organic compound may all be used as base
Matter, as long as its singlet energy is higher than illuminator, especially singlet emitters or fluorescent illuminant.
The example of the organic compound used as singlet state host material can be selected from containing aromatic hydrocarbon ring compound, such as
Benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalene is luxuriant and rich with fragrance, fluorenes, and pyrene is bent, Azulene；Heteroaromatic compound, such as dibenzo
Thiophene, dibenzofurans, dibenzoselenophene, furans, thiophene, benzofuran, benzothiophene,
Benzoselenophene, carbazole, indolocarbazole, pyridylindole, Pyrrolodipyridine, pyrazoles, miaow
Azoles, triazole, isoxazole, thiazole, oxadiazoles, oxatriazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, three
Piperazine, oxazines, oxathiazine, oxadiazine, indoles, benzimidazole, indazole, indoxazine, benzoxazoles,
Benzisoxazole, benzothiazole, quinoline, isoquinolin, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene,
Acridine, azophenlyene, phenthazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine,
Thienodipyridine, benzoselenophenopyridine and selenophenodipyridine；It include 2 to 10
The group of ring structure, they can be the aromatic hydrocarbon ring group or aromatic heterocycle group of identical or different type, and directly with one another
Or linked together by least one group below, such as oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron original
Son, chain structural unit and aliphatic cyclic group.
In a preferential embodiment, singlet state host material is optional in the chemical combination comprising at least one following group
Object:
Wherein, Ar1With the Ar in above-mentioned HIM/HTM description1And Ar2Meaning is identical, R1-R7It can select independently of each other in as follows
Group: hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl and heteroaryl, when they be virtue
Ar when base or heteroaryl, in they and above-mentioned HIM/HTM description1And Ar2Meaning is identical；
N is an integer from 0 to 20；X1-X8It selects in CH or N；X9, X10It selects in CR1R2Or NR1。
5. hole barrier materials (HBM)
Hole blocking layer (HBL) is commonly used to stop the hole from successive functional layers, especially luminescent layer.Comparison one
There is no the OLED on barrier layer, the presence of HBL normally results in the raising of luminous efficiency.The hole barrier of hole blocking layer (HBL)
Material (HBM) is needed than successive functional layers, and if the lower HOMO. of luminescent layer is in a preferential embodiment, HBM has ratio
The bigger excited level of adjacent emissive layers, such as singlet state or triplet, depending on illuminator in another preferential embodiment party
In case, HBM has electron-transport function
In one embodiment, contain molecule identical with luminescent layer mesostroma material as HBM.
In another preferential embodiment, HBM is optional in the compound comprising at least one following group:
N is an integer from 0 to 20；L is an assistant ligand；M is an integer from 1 to 3.
6. singlet emitters (Singlet Emitter)
Singlet emitters often have longer conjugated pi electron system.So far, there are many examples, such as
Styrylamine disclosed in JP2913116B and WO2001021729A1 (styrylamine) and its derivative, and in WO2008/
Indenofluorene disclosed in 006449 and WO2007/140847 (indenofluorene) and its derivative.
In a preferential embodiment, singlet emitters can be selected from unitary styrylamine
(monostyrylamines), binary styrylamine (distyrylamines), ternary styrylamine
(tristyrylamines), quaternary styrylamine (tetrastyrylamines), styrene phosphine (styrylphosphines),
Styrene ether (styryl ethers) and arylamine (arylamines).
One unitary styrylamine refers to a compound, it is comprising unsubstituted or substitution a styryl group and at least
One amine, preferably aromatic amine.One binary styrylamine refers to a compound, it includes two benzene second that are unsubstituted or replacing
Alkenyl group and at least one amine, preferably aromatic amine.One ternary styrylamine refers to a compound, it includes three unsubstituted
Or the styryl group and at least one amine, preferably aromatic amine replaced.One quaternary styrylamine refers to a compound, it is wrapped
Containing four styryl groups and at least one amine, preferably aromatic amine unsubstituted or replace.One preferred styrene is two
Styrene may be further substituted.The definition of corresponding phosphine and ethers is similar to amine.Arylamine or aromatic amine are
Refer to a kind of compound, the aromatic rings or heterocyclic ring system for directly coupling the unsubstituted of nitrogen comprising three or replacing.These aromatic series or
At least one in the loop system of heterocycle is preferentially selected in fused ring system, and is preferably formed at least 14 aromatic ring atoms.Wherein preferably
Example have a fragrant anthranylamine, fragrant anthradiamine, fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong and fragrance diamines in the wrong.One fragrance
Anthranylamine refers to a compound, and one of binary arylamine group (diarylamino) is directly linked on anthracene, preferably 9
On position.One fragrant anthradiamine refers to that a compound, wherein two binary arylamine group (diarylamino) are directly linked to
On anthracene, preferably on 9,10 position.Fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong is similar with the fragrance definition of diamines in the wrong,
Wherein binary arylamine group is preferably linked on 1 or 1,6 positions of pyrene.
The example of singlet emitters based on vinylamine and arylamine, and preferred example, can be in following patent documents
In find: WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007/
115610,US 7250532 B2,DE 102005058557 A1,CN 1583691 A,JP 08053397 A,US 6251531
B1, US 1957606 A1 of 2006/210830 A, EP and 2008/0113101 A1 of US are hereby in the above-mentioned patent document listed
Full content be incorporated herein by reference.
Example based on stibene (distyrylbenzene) extremely singlet emitters of derivative has US
5121029.
Further preferred singlet emitters are optional in indenofluorene-amine and indenofluorene-diamines, such as WO 2006/
Disclosed in 122630, benzo indenofluorene-amine (benzoindenofluorene-amine) and benzo indenofluorene-diamines
(benzoindenofluorene-diamine), as disclosed in WO 2008/006449, dibenzo indenofluorene-amine
(dibenzoindenofluorene-amine) and dibenzo indenofluorene-diamines (dibenzoindenofluorene-
Diamine), as disclosed in WO 2007/140847.
Other materials that can be used as singlet emitters have polycyclic aromatic hydrocarbon compounds, the derivative of especially following compound
Object: anthracene such as 9,10- bis- (2- naphthanthracene) (9,10-di (2-naphthylanthracene)), naphthalene, four benzene, xanthene are luxuriant and rich with fragrance
(phenanthrene), pyrene (perylene) such as 2,5,8,11-tetra-t-butylperylene, indeno pyrene
(indenoperylene), penylene (phenylenes) such as (4,4 '-(bis (9-ethyl-3-carbazovinylene) -1,
1 '-biphenyl), periflanthene, decacyclene (decacyclene), coronene (coronene), fluorenes, two fluorenes of spiral shell
(spirofluorene), aryl pyrene (arylpyrene) (such as US20060222886), arylene ethylene
(arylenevinylene) (such as US5121029, US5130603), cyclopentadiene such as tetraphenyl cyclopentadiene
(tetraphenylcyclopentadiene), rubrene (rubrene), cumarin (coumarine), rhodamine
(rhodamine), quinacridone (quinacridone), pyrans (pyrane) such as 4 (dicyanoethylene) -6- (4-
Dimethylaminostyryl-2-methyl) -4H-pyrane (DCM), thiapyran (thiapyran), bis (azinyl)
Imine-boron compound (US 2007/0092753A1), bis (azinyl) methene compound, carbostyryl chemical combination
Object, oxazinone (oxazone), benzoxazoles (benzoxazole), benzothiazole (benzothiazole), benzimidazole
(benzimidazole) and diketopyrrolopyrrole.The material of some singlet emitters can be in following patent documents
In find: US 20070252517 A1, US 4769292, US 6020078, US 2007/0252517 A1, US 2007/
0252517 A1.The full content in the above-mentioned patent document listed is incorporated herein by reference hereby.
7. triplet emitters (Triplet Emitter)
Triplet emitters are also referred to as phosphorescent emitter.In a preferential embodiment, triplet emitters be have it is logical
The metal complex of formula M (L) n, wherein M is a metallic atom, can be identical or different when L occurs every time, is one organic to match
Body, it passes through, and one or more positions are bonded or coordination is connected on metallic atom M, and n is an integer greater than 1, preferably select
It is 1,2,3,4,5 or 6.Optionally, these metal complexes are connected on a polymer by one or more positions, best
It is to pass through organic ligand.
In a preferential embodiment, metallic atom M is selected in transition metal element or lanthanide series or actinides,
Preferential selection Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag, especially preferentially selection Os, Ir, Ru,
Rh,Re,Pd,Pt。
Preferentially, triplet emitters include cheland, i.e. ligand, are matched by least two binding sites with metal
Position, what is given special priority for be triplet emitters includes two or three identical or different bidentates or multidentate ligand.Chela
Close the stability that ligand is conducive to improve metal complex.
The example of organic ligand can be selected from phenylpyridine (phenylpyridine) derivative, 7,8- benzoquinolines (7,8-
Benzoquinoline) derivative, 2 (2- thienyl) pyridines (2 (2-thienyl) pyridine) derivative, 2 (1- naphthalene) pyrroles
Pyridine (2 (1-naphthyl) pyridine) derivative or 2 phenylchinolines (2phenylquinoline) derivative.It is all these
Organic ligand may be all substituted, such as be replaced by fluorine-containing or trifluoromethyl.Assistant ligand can be preferably selected from acetic acid acetone
(acetylacetonate) or picric acid.
In a preferential embodiment, the metal complex that can be used as triplet emitters has following form:
Wherein M is a metal, is selected in transition metal element or lanthanide series or actinides；
Ar1It can be when occurring every time identical or different, be a cyclic group, wherein at least include alms giver's original
Son has the atom of a lone pair electrons, such as nitrogen or phosphorus, connected by its cyclic group and metal coordination；Ar2It can when occurring every time
It is a cyclic group to be identical or different, wherein at least includes a C atom, is connected by its cyclic group and metal
It connects；Ar1And Ar2It is linked together by covalent bond, can respectively carry one or more substituent groups, they can also pass through substitution again
Group is linked together；It can be identical or different when L occurs every time, be an assistant ligand, be preferable over double-tooth chelate ligand,
Preferably monoanionic, bidentate cheland；M is 1,2 or 3, is preferentially 2 or 3, is especially preferentially 3；N is 0,1, or 2, excellent
It is first 0 or 1, is especially preferentially 0.
The example that the material of some triplet emitters is extremely applied can be found in following patent documents and document: WO
200070655,WO 200141512,WO 200202714,WO 200215645,EP 1191613,EP 1191612,EP
1191614,WO2005033244,WO 2005019373,US 2005/0258742,WO 2009146770,WO
2010015307,WO2010031485,WO 2010054731,WO 2010054728,WO 2010086089,WO
2010099852,WO2010102709,US 20070087219 A1,US 20090061681 A1,US 20010053462
A1,Baldo,Thompson et al.Nature403,(2000),750-753,US 20090061681 A1,US
20090061681 A1,Adachi et al.Appl.Phys.Lett.78(2001),1622-1624,J.Kido et
al.Appl.Phys.Lett.65(1994),2124,Kido et al.Chem.Lett.657,1990,US 2007/0252517
A1,Johnson et al.,JACS105,1983,1795,Wrighton,JACS96,1974,998,Ma et al.,
Synth.Metals94,1998,245,US 6824895,US 7029766,US 6835469,US6830828,US
20010053462 A1,WO 2007095118 A1,US 2012004407 A1,WO 2012007088 A1,WO
2012007087 A1,WO 2012007086 A1,US 2008027220 A1,WO 2011157339 A1,
CN102282150A,WO 2009118087 A1.The full content in the above-mentioned patent document and document listed is incorporated to hereby
Herein as reference.
8. dyestuff (Dye)
In principle, all to be used for organic photovoltaic battery, including DSSC, organic functions dyestuff, can be used in the present invention
Electronic device in.Suitable dyestuff is selected from the multi-pyridine ligand of transition metal, preferably ruthenium, osmium, the metal complex dye of copper
Material.In a preferred embodiment, the general structure ML2 (X) 2 of metal complex dyes, wherein L is preferably selected from 2,2'- connection
In pyridine -4,4'- dicarboxylic acids, M is transition metal, and excellent dyestuff is selected from Ru, Os, Fe, and V and Cu, X are selected from halide, cyaniding
The substituent group of object, rhodanate, acetylacetonate compound, thiocarbamate or water.These premetallized dyes are following
Document in be disclosed The Journal of Physical Chemistry C2009,113,2966-2973,
US2009000658,WO2009107100,WO2009098643,US6245988,WO2010055471,JP2010084003,
EP1622178,WO9850393,WO9529924,WO9404497,WO9214741,WO9116719.It is listed hereby by above-mentioned
Full content in patent document and document is incorporated herein by reference.
Below in conjunction with preferred embodiment, the present invention is described, but the present invention is not limited to the following examples,
It is answered it should be understood that appended claims summarise the scope of the present invention those skilled in the art under the guidance of present inventive concept
Recognize, to certain change that various embodiments of the present invention are carried out, all by by claims of the present invention spirit and
Range is covered.
Specific embodiment
1. the material and composition that use
The synthesis of illuminator 1 and main body 1 can be found in Chinese patent application CN102668152 and its bibliography.
Sulfolane and 3,4- dimethylanisole are purchased from Sigma-Aldrich.
Composition below is heated (60 DEG C) and is filtered obtained by stirring.Wherein F1, F3 are reference portfolios object, F2, F4
It is composition according to the invention.
| Organic functional material [weight ratio] | Solvent [volume ratio] | Concentration [g/L] | |
| F1 | Illuminator 1: main body 1 (1:4) | 3,4-DMA | 1,5 |
| F2 | Illuminator 1: main body 1 (1:4) | 3,4-DMA:Sulfolane(1:1) | 1,5 |
| F3 | Illuminator 1: main body 1 (1:4) | 3,4-DMA | 2,8 |
| F4 | Illuminator 1: main body 1 (1:4) | 3,4-DMA:Sulfolane(1:1) | 2,8 |
2. printing test
Substrate is PET film, is handled using preceding cleaning, and with UV/Ozone.
F1, F2 ink are printed using Dimatix DMP2800 printing ink.10 milli of drop spacing (ds) printing is fallen using 30
The square of rice.It is dry using one hour of vacuum at room temperature, evaluate the difference of film quality.The filming performance of F1 is very poor,
And the filming performance of F2 is good.
F3, F4 ink are printed using intaglio printing.Use 100 rows/cm intaglio plate, the square of 10 millimeters of printing.It uses
One hour of vacuum is dry at room temperature, evaluates the difference of film quality.The filming performance of F3 is very poor, and the filming performance of F4 is equal
It is even good.
Claims (10)
1. a kind of composition is a solution, it includes have sulfolane (Sulfolane) or dimethyl sulfone (Dimethyl
Sulfone) and one or more organic functional materials, it is characterised in that: 1) at least a kind of organic functional material is small molecule
Material；2) viscosity of the composition at 25 DEG C is within the scope of 1.5 to 40mPs；3) conduct of neutral high polymer material is not included
Additive.
2. composition according to claim 1 also includes one or more organic solvents.
3. composition according to claim 1, one or more of them organic functional material is selected from hole-injecting material
(HIM) hole mobile material (HTM) or electron-blocking materials (EBM) or their various combinations.
4. composition according to claim 1, one or more of them organic functional material is selected from electron injection material
(EIM) electron transport material (ETM) or hole barrier materials (HBM) or their various combinations.
5. composition according to claim 1 includes an organic luminorphor and an organic host material.
6. composition according to claim 5, organic luminorphor is fluorescent illuminant or phosphorescent emitter.
7. composition according to claim 1, it is characterised in that viscosity at 25 DEG C of the composition is 2.5 to 30mPs
In range.
8. the purposes that composition according to claim 1 is used to prepare organic electronic device as coating or printing ink.
9. a kind of organic electronic device includes one or more layers organic functional thin film, wherein at least having thin film is from root
It prepares according to composition described in claim 1, is prepared especially by the method for printing or coating.
10. organic electronic device according to claim 9 can be selected from Organic Light Emitting Diode, organic light emission battery, organic photovoltaic
Battery, organic field-effect tube, organic light-emitting field effect pipe, organic sensor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410289452.6A CN104282834B (en) | 2013-07-07 | 2014-06-25 | A kind of composition and its application in organic electronic device |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310285265.6 | 2013-07-07 | ||
| CN201310285265 | 2013-07-07 | ||
| CN2013102852656 | 2013-07-07 | ||
| CN201410289452.6A CN104282834B (en) | 2013-07-07 | 2014-06-25 | A kind of composition and its application in organic electronic device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104282834A CN104282834A (en) | 2015-01-14 |
| CN104282834B true CN104282834B (en) | 2019-06-14 |
Family
ID=52257517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410289452.6A Active CN104282834B (en) | 2013-07-07 | 2014-06-25 | A kind of composition and its application in organic electronic device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104282834B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180327622A1 (en) * | 2015-11-12 | 2018-11-15 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing formulation and application thereof |
| US11248138B2 (en) * | 2016-11-23 | 2022-02-15 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink formulations, preparation methods and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102668152A (en) * | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | Compositions comprising polymeric binders |
| CN102827507A (en) * | 2011-06-17 | 2012-12-19 | 富士胶片株式会社 | Ink set and image forming method |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5799596A (en) * | 1995-05-19 | 1996-11-29 | Uniax Corporation | Electrochemical light-emitting devices |
| DE10238903A1 (en) * | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | New heteroaromatic rhodium and iridium complexes, useful in electroluminescent and/or phosphorescent devices as the emission layer and for use in solar cells, photovoltaic devices and organic photodetectors |
| JP4415653B2 (en) * | 2003-11-19 | 2010-02-17 | セイコーエプソン株式会社 | Thin film transistor manufacturing method |
| US8183319B2 (en) * | 2007-10-31 | 2012-05-22 | Air Products And Chemicals, Inc. | Film forming additive formulations of conductive polymers |
| WO2011128035A1 (en) * | 2010-04-12 | 2011-10-20 | Merck Patent Gmbh | Composition and method for preparation of organic electronic devices |
-
2014
- 2014-06-25 CN CN201410289452.6A patent/CN104282834B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102668152A (en) * | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | Compositions comprising polymeric binders |
| CN102827507A (en) * | 2011-06-17 | 2012-12-19 | 富士胶片株式会社 | Ink set and image forming method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104282834A (en) | 2015-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103985822B (en) | Organic mixture, composite containing organic mixture, organic electronic device and application | |
| CN107004777B (en) | Polymer includes its mixture, composition, organic electronic device and monomer | |
| CN108368045A (en) | Thermal excitation delayed fluorescence material, high polymer, mixture, composition and organic electronic device | |
| CN104277063B (en) | A kind of compound based on borazine and the application in organic electronic device | |
| CN107001380A (en) | Compound, the mixture comprising it, composition and organic electronic device | |
| CN107406384A (en) | The organic compound of deuterate, the mixture comprising the compound, composition and organic electronic device | |
| CN109608504A (en) | Organometallic complex, polymer, mixture, composition and organic electronic device | |
| CN107004778B (en) | Organic mixture, composition containing organic mixture, organic electronic device and application | |
| CN107004779B (en) | Organic compound, mixture, composition and organic electronic device comprising it | |
| CN107108862B (en) | Conjugated polymer, the mixture comprising it, composition, organic electronic device and its application of the crosslinked group containing acetenyl | |
| CN107001336A (en) | A kind of organometallic complex, the polymer comprising it, mixture, composition, organic electronic device and application | |
| CN109638171A (en) | Organic mixture, high polymer, composition and application thereof | |
| CN108137634A (en) | A kind of metal organic complex and its application in electronic device | |
| CN108137622A (en) | Siliceous organic compound and its application | |
| CN109790461A (en) | Mixture, composition and organic electronic device | |
| CN110746442A (en) | Imidazole spiro-containing compound and application thereof | |
| CN109790193A (en) | Transient metal complex and its application, mixture, organic electronic device | |
| CN108137558A (en) | Carbazole derivates, high polymer, mixture, composition, organic electronic device and its application | |
| CN109791992B (en) | High polymers, mixtures, compositions and organic electronic devices comprising the same, and monomers for polymerization | |
| CN110872313A (en) | Compound containing silicon spiro structure and application thereof | |
| CN109400586A (en) | Organic compound, mixture, high polymer, composition containing luxuriant and rich with fragrance carbazole and pyridines and application thereof | |
| CN109705100A (en) | The organic optical compounds of carbazoles containing naphthalene, mixture, composition and application thereof | |
| CN109790183A (en) | Metal organic complex and its application, mixture, organic electronic device | |
| CN104277538B (en) | A kind of includes the composition of stabilizer and its application in organic electronic device | |
| CN108349890A (en) | It is used to prepare organic functions chemical combination object and its application of organic electronic device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20210106 Address after: 148 Yongda Road, Huangyan District, Taizhou City, Zhejiang Province 318020 Patentee after: Zhejiang Guanghao Photoelectric Technology Co.,Ltd. Address before: 318057 No.93, area 3, Panjia village, Jinqing Town, Luqiao District, Taizhou City, Zhejiang Province Patentee before: Pan Caifa |