CN103996795A - Organic luminous element - Google Patents
Organic luminous element Download PDFInfo
- Publication number
- CN103996795A CN103996795A CN201310052201.1A CN201310052201A CN103996795A CN 103996795 A CN103996795 A CN 103996795A CN 201310052201 A CN201310052201 A CN 201310052201A CN 103996795 A CN103996795 A CN 103996795A
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- Prior art keywords
- aryl
- organic
- heteroaryl
- layer
- group
- Prior art date
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- 239000010410 layer Substances 0.000 claims abstract description 87
- 239000000758 substrate Substances 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- -1 heterocyclic radical Chemical class 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000011247 coating layer Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000008378 aryl ethers Chemical class 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 150000004832 aryl thioethers Chemical class 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 150000003004 phosphinoxides Chemical class 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000001725 pyrenyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 abstract description 8
- 239000004973 liquid crystal related substance Substances 0.000 abstract 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 description 79
- 150000001875 compounds Chemical class 0.000 description 31
- 238000000034 method Methods 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 239000002019 doping agent Substances 0.000 description 17
- 230000027756 respiratory electron transport chain Effects 0.000 description 17
- 230000005540 biological transmission Effects 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
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229920003026 Acene Polymers 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 241001597008 Nomeidae Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005566 electron beam evaporation Methods 0.000 description 4
- 229910001092 metal group alloy Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 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
- 238000007747 plating Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 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 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- SCHRRICRQNJJKN-UHFFFAOYSA-N P.[O] Chemical compound P.[O] SCHRRICRQNJJKN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910003472 fullerene Inorganic materials 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000005054 naphthyridines Chemical class 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 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
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- OQCFWECOQNPQCG-UHFFFAOYSA-N 1,3,4,8-tetrahydropyrimido[4,5-c]oxazin-7-one Chemical compound C1CONC2=C1C=NC(=O)N2 OQCFWECOQNPQCG-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- UPCSDGIBZSWQEQ-UHFFFAOYSA-N 10H-phenoxazine thiophene Chemical compound C=1C=CSC=1.C1=CC=C2NC3=CC=CC=C3OC2=C1 UPCSDGIBZSWQEQ-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical group C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- WLODWTPNUWYZKN-UHFFFAOYSA-N 1h-pyrrol-2-ol Chemical class OC1=CC=CN1 WLODWTPNUWYZKN-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- CRHRWHRNQKPUPO-UHFFFAOYSA-N 4-n-naphthalen-1-yl-1-n,1-n-bis[4-(n-naphthalen-1-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 CRHRWHRNQKPUPO-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UJRPSSCGWJWRIB-UHFFFAOYSA-N C1(=CC=C2C=CC3=CC=CC4=CC=C1C2=C34)[PH2]=O Chemical class C1(=CC=C2C=CC3=CC=CC4=CC=C1C2=C34)[PH2]=O UJRPSSCGWJWRIB-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- MVORZMQFXBLMHM-QWRGUYRKSA-N Gly-His-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 MVORZMQFXBLMHM-QWRGUYRKSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
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- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
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- 150000004056 anthraquinones Chemical class 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XCJXQCUJXDUNDN-UHFFFAOYSA-N chlordene Chemical compound C12C=CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl XCJXQCUJXDUNDN-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
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- 150000004696 coordination complex Chemical class 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 210000004276 hyalin Anatomy 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002632 lipids Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical class C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
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- 125000001979 organolithium group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
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- 229920000767 polyaniline Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
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- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical group N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical class C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000985 reflectance spectrum Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/302—Details of OLEDs of OLED structures
- H10K2102/3023—Direction of light emission
- H10K2102/3026—Top emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/875—Arrangements for extracting light from the devices
- H10K59/879—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic luminous element. A substrate, a first electrode, a luminous layer containing more than one organic layer film, a second electrode emitting light through the abovementioned luminous layer, an organic covering layer are formed in sequence, wherein the organic covering layer contains a phosphine oxide derivative. The organic luminous element provided by the invention can realize high luminous efficiency and color reproducibility, and can be used for light sources, marking plates, identification lamps of backlight sources of organic EL displays and liquid crystal displays, lighting devices and gauges.
Description
Technical field
The present invention relates to organic illuminating element, particularly increase substantially the organic illuminating element of the taking-up efficiency of light.
Background technology
Organic illuminating element is self-emission display apparatus, has the features such as light and slim, wide viewing angle, low driving voltage, high brightness luminescent.
Conventionally, to be the hole of electrode injection and electronics produce light when transitting to ground state by excitation state at luminescent layer to the luminous principle of organic illuminating element again.The feature of this element is slim, and high brightness luminescent under low driving voltage is luminous by selecting different luminescent materials to produce different multiple colors, therefore receives much attention.
This research, since the C.W.Tang by Kodak etc. has disclosed organic thin film device high brightness luminescent, has been carried out investigation widely for its application, and wherein organic film light-emitting component is applied in employings such as mobile phone display screens.But also have a lot of technical problems, especially realizing high-luminous-efficiency low driving voltage organic illuminating element is a problem.
The direction emitting beam according to organic luminous layer, organic illuminating element can be divided into end transmitting organic illuminating element and top transmitting organic illuminating element.In end transmitting organic illuminating element, light sends towards substrate, and reflecting electrode is formed on organic luminous layer, and transparency electrode is formed under organic luminous layer.If organic illuminating element is the organic illuminating element of active matrix, the not transmitted ray of film crystal tube portion wherein forming, so light-emitting area reduces.On the other hand, in top transmitting organic element, transparency electrode is formed on organic luminous layer, and reflecting electrode is formed under organic luminous layer, thus light send to substrate rightabout, thereby increased light transmission area and improved brightness.
In prior art, in order to improve the luminous efficiency of top transmitting organic illuminating element, adopt such as forming organic coating layer on semi-transparent metals electrode above through luminescent layer is radiative, regulate optical interference distance, suppress external light reflection, suppress surface plasma physical efficiency and move the methods such as the delustring that causes, be documented in patent documentation 1, patent documentation 2, patent documentation 3, patent documentation 4, patent documentation 5.
For example, patent documentation 2 has been recorded above top transmitting organic illuminating element and has been formed organic coating layer on semi-transparent metals electrode, has improved the luminous efficiency of red emission light and the green emitted light organic illuminating element of approximately 1.5 times.It is amine derivative that organic coating layer uses material, qualone derivative etc.
The organic coating layer Effect of Materials blue emission light that patent documentation 4 has been recorded energy gap 3.2eV left and right is not suitable for organic coating layer material, and the organic coating layer material of use is the amine derivative etc. with specific chemical constitution.
Patent documentation 5 has been recorded and has been realized low CIEy value blue emission light organic illuminating element, organic coating layer material is △ n>0.08 at the index of refraction variable quantity of wavelength 430nm-460nm, and the organic coating layer material of use is anthracene derivant having specific chemical constitution etc.
Patent documentation
Patent documentation 1:WO2001/039554
Patent documentation 2:JP2006-156390
Patent documentation 3:JP2007-103303
Patent documentation 4:JP2006-302878
Patent documentation 5:WO2011/043083.
Summary of the invention
As mentioned above, the amine derivative etc. that prior art is organic coating layer materials'use has an ad hoc structure of high refractive index has improved light and has taken out efficiency, colourity, but do not solve the problem of ageing stability simultaneously.
The invention provides a kind of organic coating layer materials'use phosphinoxide, solve and improve light taking-up efficiency, when improving colourity, solve the problem of ageing stability.
The invention provides a kind of organic illuminating element, substrate, the first electrode, the luminescent layer that contains more than one organic tunics, sees through radiative the second electrode of aforementioned light emission layer, and the order successively of organic coating layer forms, and wherein, organic coating layer contains phosphinoxide.
Be greatly improved luminous taking-up efficiency and there is the organic illuminating element of superior ageing stability of the present invention.
Index of refraction shown in Lorentz-Lorent formula is that polarizability and density are directly proportional.The material index of refraction that polarizability and density are large is larger.
N: refractive power
, λ: light irradiation wavelength, P: polarization
, V: molecular volume
The inventor finds that phosphine oxygen base P=O key has high polarizability feature, and phosphinoxide can obtain high refractive index, uses and in organic coating layer, can improve light taking-up efficiency.
Phosphinoxide in the present invention, shown in general formula specific as follows (1).
Wherein, R
1～R
3can be identical or different, be selected from respectively hydrogen, halogen or without one or more in the alkyl, cycloalkyl, heterocyclic radical, alkenyl, cycloalkenyl group, alkynyl, alkoxyl, alkylthio group, aryl ether, aryl thioethers base, aryl, heteroaryl, amino or the silicyl that replace or replace, wherein R
1～R
3at least one is without the aryl or the heteroaryl that replace or replace, the integer that n is 1-4; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
Described halogen atom is selected from fluorine, chlorine, bromine or iodine.
Described alkyl is preferably the alkyl of C1-C15; More preferably one or more in the representative examples of saturated aliphatic alkyl such as methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl or tert-butyl group.Abovementioned alkyl can have substituting group and also can there is no substituting group.
Described cycloalkyl is preferably the cycloalkyl of C3-C20; More preferably one or more in the saturated fat ring type alkyl such as cyclopropyl, cyclohexyl, norborny or adamantyl.Above-mentioned cycloalkyl can have substituting group and also can there is no substituting group.
Described heterocyclic radical is preferably the heterocyclic radical of C3-C20; More preferably in the ring such as pyranoid ring, piperidine ring or cyclic amide, there are one or more in the aliphat ring of the atom beyond carbon.Above-mentioned heterocyclic radical can have substituting group and also can there is no substituting group.
Described alkenyl is preferably the alkenyl of C2-C20; More preferably vinyl, pi-allyl or butadienyl etc. are wrapped one or more in double bond containing unsaturated fatty hydrocarbons base.Above-mentioned alkenyl can have substituting group and also can there is no substituting group.
Described cycloalkenyl group is preferably the cycloalkenyl group of C4-C20; More preferably cyclopentenyl, cyclopentadienyl group or cyclohexenyl group etc. wrap one or more in double bond containing unsaturated lipid ring type alkyl.Above-mentioned cycloalkenyl group can have substituting group and also can there is no substituting group.
Described alkynyl is preferably the alkynyl of C2-C20; The unsaturated fatty hydrocarbons base that more preferably acetenyl etc. comprises triple bond.Above-mentioned alkynyl can have substituting group and also can there is no substituting group.
Described alkoxyl is preferably the alkoxyl of C1-C60; More preferably methoxyl group, ethyoxyl or propoxyl group etc. are situated between by one or more in the functional group of ehter bond bonding aliphatic alkyl.This aliphatic alkyl can have substituting group and also can there is no substituting group.
Described alkylthio group is the group that the oxygen atom of alkoxyl is replaced into sulphur atom.Be preferably the alkylthio group of C1-C60; The alkyl of alkylthio group can have substituting group and also can there is no substituting group.
Described aryl ether is preferably the aryl ether of C6-C40; More preferably phenoxy group etc. is situated between by the functional group of ehter bond bonding aromatic hydrocarbyl.Aryl ether can have substituting group and also can there is no substituting group.
The oxygen atom that described aryl thioethers base is the ehter bond of aryl ether is replaced into the group of sulphur atom.Be preferably the aryl thioethers base of C6-C40.Aromatic hydrocarbyl in aryl thioethers base can have substituting group and also can there is no substituting group.
Described silicyl representation case has and the functional group of the key of silicon atom bonding as trimethyl silyl etc., and silicyl can have substituting group and also can there is no substituting group.Silicyl carbon number is not particularly limited, and is generally more than 3 scope below 20.In addition, silicon number is generally more than 1 scope below 6.
Described amino can have substituting group and also can there is no substituting group.Amino substituting group carbon number is not particularly limited, and is generally more than 2 scope below 60.
Described aryl is preferably the aryl of C6-C60; More preferably phenyl, naphthyl, xenyl, anthryl, pyrenyl, 9, one or more in the aromatic hydrocarbyls such as 9-fluorenyl, phenanthryl, benzo phenanthryl, benzo ［ a ］ anthryl, benzene terphenyl, acenaphthylene base, Pi base or perylene base.Aryl can have substituting group and also can there is no substituting group.
Described heteroaryl is preferably the aromatic heterocycle of C5-C60; More preferably one or more in furyl, benzofuranyl, two acene furyls, thienyl, benzothienyl, two acene thienyls, quinolyl, isoquinolyl, quinazolyl, cinnolines base, phthalazinyl, acridinyl, phenanthridinyl, oxa-anthryl, phenazinyl, phenoxazine thiophene base, phenoxazine group, thianthrene group, benzopyranyl, different benzopyranyl, carbazyl or benzimidazole etc.Aromatic heterocycle can have substituting group and also can there is no substituting group.
The phosphine oxygen base of phosphinoxide shown in general formula (1) replaces different substituting group groups, can obtain superior thin film stability.
As mentioned above, phosphinoxide has high refractive index, and organic coating layer materials'use has phosphinoxide, and the light that is improved takes out efficiency and superior thin film stability can obtain the organic illuminating element that ageing stability is existed side by side.
From synthetic simplicity, when the vapour deposition method maskings such as organic coating layer materials'use resistance heating evaporation, thermal endurance viewpoint is considered, in above-mentioned general formula (1), and n more preferably 1 or 2.
Consider that high glass transition temperature can obtain more superior thin film stability, in above-mentioned general formula (1), R
1more preferably aryl, substituted aryl, heteroaryl or substituted heteroaryl; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
As the compound shown in above-mentioned general formula (1), be not particularly limited the example that specifically can be listed below.
Further be preferably from index of refraction viewpoint heteroaryl two acene thienyls, carbazyl or the two acene furyls that replacement also can not replace.
More preferably replace from suppressing crystallization viewpoint aryl the xenyl, naphthyl, fluorenyl, anthryl or the pyrenyl that also can there is no replacement.Further consider from index of refraction and thin film stability viewpoint, aryl is further preferably replacement can not have the fluorenyl or the pyrenyl that replace yet.Most preferably be pyrenyl or replace pyrenyl.Substituting group as described above.
Thereby, in above-mentioned general formula (1), R
1most preferably be pyrenyl or replace pyrenyl; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.And then consider from improving glass transition temperature viewpoint, in above-mentioned general formula (1), R
2, R
3in at least one more preferably aryl, substituted aryl, heteroaryl or substituted heteroaryl; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
The synthetic of phosphinoxide shown in general formula (1) can be used known method.Enumerate for example halo phosphinoxide and RMgBr or the substitution reaction of organolithium reagent, two replacement phosphinoxide and halogenated aryl coupling reactions under palladium catalyst exists, the oxidation reaction of phosphorus compound etc., but do not limit and these methods.
Illustrate organic illuminating element example of the present invention.Organic illuminating element of the present invention is substrate, the first electrode, and the luminescent layer that contains more than one organic tunics, sees through radiative the second electrode of aforementioned light emission layer, and the order successively of organic coating layer forms, and this luminescent layer is electric energy and luminous.
Light-emitting component of the present invention preferably uses the glass substrate such as soda-lime glass or alkali-free glass.For the thickness of glass substrate, as long as there is sufficient thickness in order to keep mechanical strength, as long as be that 0.5mm is above just enough.For the material of glass, from glass, the ion of stripping is more few better, therefore, and preferably alkali-free glass.Or, because implemented SiO
2also there is sale in the soda lime market of protective coating, therefore also can use this commercially available product.And then if the first electrode plays consistently function, substrate it be not necessary for glass, for example, also can on plastic base, form anode.
For the material of the first electrode, be preferably and there is the metal such as gold, silver, aluminium of high refractive index characteristic or these metal alloys or APC and be associated gold.These metal or metal alloy can be also multilayer laminated.And then metal, metal alloy or these layers are above and/or can be also the transparent conductive metal oxides such as multilayer laminated tin oxide, indium oxide, indium tin oxide target (ITO) or indium zinc oxide below.
For the material of the second electrode, be preferably the material of the translucent or hyaline membrane that forms light transmission.For example, the transparent conductive metal oxide such as silver, magnesium, aluminium, calcium or these metal alloys, tin oxide, indium oxide, indium tin oxide target (ITO) or indium zinc oxide.These metals, alloy or metal oxide can be also multilayer laminated.
Above-mentioned electrode forming method can be also resistance heating evaporation, electron beam evaporation plating, sputter, ion plating or glue rubbing method etc., is not particularly limited.And then the first electrode and the second electrode be, the material work function of use, any electrode is anode, another kind is negative electrode.
Organic layer, except only comprising the formation of luminescent layer, also can enumerate 1) hole transmission layer/luminescent layer, 2) luminescent layer/electron transfer layer, 3) hole transmission layer/luminescent layer/electron transfer layer, 4) hole injection layer/hole transmission layer/luminescent layer/electron transfer layer, 5) hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer etc.And then above-mentioned each layer can be that various individual layers can be also multilayers.Form 1)～5) each layer time, anode electrode contacts with hole input layer or hole transmission layer, cathode electrode contacts with electron transfer layer with electronics input layer in addition.
Hole transmission layer, can be by by method stacked one or two or more kinds of hole mobile material or that mix, or forms by the method for the mixture of hole mobile material and polymer binder.Hole mobile material need to effectively transmit from anodal hole between the electrode that has applied electric field, therefore wishes that hole injection efficiency is high, effectively transmits injected holes.Therefore requiring hole mobile material is to have suitable ionic potential, and hole mobility is large, and then excellent in stability, is not easy to produce the material of impurity that becomes trap when manufacture and while use.As the material that meets such condition, be not particularly limited, for example 4,4 '-bis-(N-(3-aminomethyl phenyl)-N-phenyl aminos) biphenyl (TPD), 4,4 '-bis-(N-(1-naphthyl)-N-phenyl aminos) biphenyl (NPD), 4,4 '-bis-(N, N-xenyl) amino) biphenyl (TBDB), or two (N, N-diphenyl-4-phenyl amino)-N, N-diphenyl-4,4 '-diaminostilbene, the benzidine such as 1 '-biphenyl (TPD232), 4,4 ', 4 ' '-tri-(3-aminomethyl phenyl (phenyl) amino) triphenylamine (m-MTDATA), or 4, the triphenylamine derivatives such as 4 ', 4 ' '-tri-(1-naphthyl (phenyl) amino) triphenylamine (1-TNATA), have the material of carbazole structure, wherein be preferably carbazoles polymer, specifically can enumerate two carbazole derivates such as two (N-aryl carbazoles) or two (N-alkyl carbazoles), three carbazole derivates, four carbazole derivates, three benzene compounds, pyrazoline derivative, stilbene based compound, hydrazine based compound, benzofuran derivatives, thiophene derivant, oxadiazoles derivative, phthalocyanine, the heterocyclic compounds such as porphyrin, or fullerene derivate, in polymer system, side chain has Merlon or the ethene derivatives of above-mentioned monomer, polythiophene, polyaniline, poly-fluorenes, Polyvinyl carbazole or polysilane etc.And then, also can use P type Si, the inorganic compounds such as P type SiC.
Anode and hole transport interlayer also can have hole injection layer.Make organic illuminating element there is hole injection layer and realize low driving voltage, improve endurance life.Hole injection layer is generally the preferably material lower than the ionic potential of hole transport layer material.For example illustrate, above-mentioned such as TPD232 benzidine derivative, triphenylamine material group, also can be used phthalocyanine derivates in addition.Hole injection layer also can be independent acceptor compound form, can also acceptor is compound doped use at hole transmission layer.Acceptor compound for example can be enumerated, the metal oxides such as metal chloride, molybdenum oxide, vanadium oxide, tungsten oxide or ruthenium-oxide such as ferric trichloride (III), aluminium chloride, gallium chloride, inidum chloride or antimony chloride, the electric charges such as three (4-bromophenyl) chlordene ammonium antimonate shift coordination thing.And then can be also organic compound, quinone based compound, acid anhydrides based compound or the fullerene etc. in molecule with nitro, cyano group, halogen or trifluoromethyl.
In the present invention, luminescent layer can be individual layer, and any of multilayer can utilize respectively luminescent material (material of main part, dopant material) to form, and it can be the mixture of material of main part and dopant material, can be also only material of main part, and arbitrary situation can.That is, in light-emitting component of the present invention, in each luminescent layer, can be material of main part or only dopant material is luminous only, can be also material of main part is luminous together with dopant material.From effectively utilizing electric energy, obtain the luminous viewpoint consideration of high color purity, preferably luminescent layer is made up of the mixing of material of main part and dopant material.In addition, material of main part and dopant material can be respectively a kind of can be also multiple combinations, arbitrary situation can.Dopant material can be comprised also and can partly be comprised by whole material of main part, and arbitrary situation can.Dopant material can stackedly also can be dispersed, and arbitrary situation can.Dopant material can be controlled illuminant colour.When the amount of dopant material is too much, concentration frosting phenomenon can occur, therefore, the relative material of main part of its consumption is preferably below 20 % by weight, more preferably below 10 % by weight.For doping method, can utilize with the common vapour deposition method of material of main part and form, after also can mixing with material of main part in advance, carry out evaporation.
Luminescent material, particularly, at present as the known fused-ring derivatives such as anthracene or pyrene of luminous element, metal chelating combination hydroxyquinoline compounds, two benzofuran derivs, carbazole derivates or indolocarbazole derivative taking three (oxine) aluminium as representative, polymer can use polyphenylene vinylene derivative, poly radical derivative or polythiofuran derivative etc., is not particularly limited.
The contained material of main part of luminescent material is not particularly limited, can use anthracene, luxuriant and rich with fragrance, pyrene, benzophenanthrene, aphthacene, perylene, benzo ［ 9, 10 ］ phenanthrene, fluoranthene, fluorenes, or indenes etc. has the compound or derivatives thereof of condensation aryl rings, N, N '-dinaphthyl-N, N '-diphenyl-4, 4 '-diphenyl-1, the aromatic amine derivatives such as 1 '-diamines, metal chelating combination hydroxyquinoline compounds taking three (oxine) aluminium as representative, Pyrrolopyridine derivatives, two acene furan derivatives, carbazole derivates, indolocarbazole derivative, pyrrolotriazine derivatives, polymer can use polyphenylene vinylene derivative, poly radical derivative, poly-fluorene derivative, Polyvinyl carbazole derivative, or polythiofuran derivative etc., be not particularly limited.
Dopant material is not particularly limited, can enumerate naphthalene, anthracene, luxuriant and rich with fragrance, pyrene, benzophenanthrene, perylene, benzo ［ 9, 10 ］ phenanthrene, fluoranthene, fluorenes, indenes etc. have the compound or derivatives thereof (for example 2-(benzothiazole-2-yl)-9 of thick aromatic ring, 10-diphenylanthrancene etc.), furans, pyrroles, thiophene, thiophene is coughed up, 9-sila thing, 9, 9 '-spiral shell, two silicon heterofluorenes, benzothiophene, benzofuran, indoles, two acene thiophene, two acene furans, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridines, quinoxaline, pyrrolopyridine, or thioxanthene etc. has the compound or derivatives thereof of heteroaryl ring, borane derivative, diphenylethyllene benzene derivative, aminobenzene ethenyl derivatives, pyrroles's methine derivative, diketo pyrrolo-［ 3, 4-c ］ azole derivatives, coumarin derivative, imidazoles, thiazole, thiadiazoles, carbazole, oxazole, oxadiazole, the Zole derivatives such as triazole, or aromatic amine derivative etc.
In addition, the luminescent layer phosphorescent light-emitting materials that also can adulterate.Phosphorescent light-emitting materials is also can the luminous material of phosphorescence under room temperature.Phosphorescent light-emitting materials is used in the situation of dopant, is substantially necessary that at room temperature phosphorescence is luminous, but is not particularly limited that the preferably group of indium, ruthenium, rhodium, palladium, platinum, osmium or rhenium composition at least contains a kind of Organometallic complex compound of metal.From room temperature, there is high phosphorescence luminous efficiency viewpoint and consider more preferably there is the Organometallic complex compound of indium or platinum.The preferred indole derivatives of material of main part of phosphorescence photism dopant and use, carbazole derivates, or indolocarbazole derivative, there is pyridine, pyrimidine, or the nitrogen-containing aromatic compound derivative of triazine structure, polyaryl benzene derivative, volution fluorene derivative, three polyindenes, benzo ［ 9, 10 ］ the luxuriant and rich with fragrance arene compound derivative that waits, two acene furan derivatives, or two compound of containing oxygen group elements such as acene thiophene, or the organic metal coordination thing such as oxyquinoline beryllium complex, substantially the material of main part using can be that triplet can be greater than dopant triplet energy, electronics and hole are from round and smooth injection or the transmission of layer input layer separately, be not particularly limited.In addition, can contain two or more triplet light-emitting dopant, also can contain two or more material of main part.And then contain more than one triplet light-emitting dopants and more than one fluorescent light-emitting dopants.
In the present invention, electron transfer layer is for to be injected into electronics from negative electrode, and then the layer that electronics is transmitted.The electron injection efficiency of wishing electron transfer layer is high, the electronics that effectively transmission is injected into.Therefore, require that the electron affinity of electron transfer layer is large and electron mobility is large, and then excellent in stability, when manufacture and be not easy to produce the material of the impurity that becomes trap while use.But, in the time of the transmission equilibrium of Considering Cavitation Effects and electronics, if mainly bringing into play, electron transfer layer can effectively stop the effect that flows to cathode side from the hole of anode in the situation that there is no combination again, even if be made up of the so not high material of electron transport ability, the effect of improving luminous efficiency also can be equal with situation about being made up of the high material of electron transport ability.Thereby, in the electron transfer layer in the present invention, also comprise and the material of hole trapping layer synonym that can effectively stop hole migration.
The electron transport material using in electron transfer layer is not particularly limited, can list naphthalene, or anthracene etc. has thick aromatic derivatives, with 4, the styrene aromatic derivatives that 4 '-bis-(diphenylacetylene) biphenyl is representative, the derivative such as anthraquinone or diphenoquinone, phosphinoxide, the oxyquinoline complex compounds such as three (oxine) aluminium, Qiang base Ben Ji oxazole complex compound, hydroxyl azoles complex compound, azomethine complex compound, tropolone metal complex or flavonols metal complex, from reducing the viewpoint of driving voltage, preferably use the compound with heteroaryl ring structure, described hetero-aromatic ring structure is by being selected from carbon, hydrogen, nitrogen, oxygen, element in silicon or phosphorus forms and containing electronics acceptance nitrogen.
The hetero-aromatic ring that contains electronics acceptance nitrogen has high electron affinity.Be used in the electron transfer layer that contains electronics acceptance nitrogen, there is the acceptant electronics of high electron affinity electrode, can reduce the driving voltage of light-emitting component.Large to luminescent layer electron transport ability, luminescent layer again combination ratio increase and improve luminous efficiency.The hetero-aromatic ring that contains electronics acceptance nitrogen, for example can enumerate pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridines ring, pyrimido pyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, oxadiazole rings, triazole ring, thiazole ring, Thiadiazole, benzoxazole ring, benzothiazole ring, benzimidazole ring or phenanthro-imidazole ring etc.
In addition, the compound that has hetero-aromatic ring structure as these, can list the oligomeric pyridine derivates such as such as benzimidizole derivatives, benzoxazole derivative, benzothiazole derivant, oxadiazole derivative, thiadiazoles derivative, triazole derivative, pyrazines derivatives, phenanthroline derivative, quinoxaline derivant, quinoline, benzoquinoline derivative, bipyridine or terpyridyl.Said derivative has thick aromatic ring structure, improves glass transition temperature, and electron mobility increases, and improves the effect of the low driving voltage of light-emitting component.And then, improve light-emitting component endurance life, synthetic simple, raw material is easily bought consideration, preferably has the thick aromatic ring of anthracene structure, pyrene structure or phenanthroline structure.
Above-mentioned electron transport material can use separately, also two kinds of above above-mentioned electron transport materials can be mixed and uses, or more than one other electron transport material is mixed in above-mentioned electron transport material and is used.Also can be donor compound in addition.Donor compound is by improving electronic injection obstacle, electronics easily to be injected to electron transfer layer from negative electrode or electron injecting layer, and then improves the compound of the electrical conductivity of electron transfer layer.As the preference of donor compound of the present invention, can enumerate: alkali metal, the inorganic salts or alkaline-earth metal and the organic complex compound etc. that contain alkali-metal inorganic salts, alkali metal and organic complex compound, alkaline-earth metal or contain alkaline-earth metal.As the preferred kind of alkali metal or alkaline-earth metal, can enumerate low work function and improve the alkali metal of lithium, sodium or caesium that the effect of electron transport ability is large and so on or the alkaline-earth metal of magnesium or calcium and so on.
In the present invention, negative electrode and electric transmission interlayer also can have electron injecting layer.Generally, electron injecting layer is that the electronic injection being conducive to from negative electrode to electron transfer layer is object, and electronic injection layer material can be the hetero-aromatic ring that contains electronics acceptance nitrogen, can be also above-mentioned donor compound.In addition, can be also insulator and semiconductor inorganic matter.Use these materials can effectively prevent short circuit, and can improve electronic injection.These insulators are for example selected from, alkali metal chalkogenide, and alkaline-earth metal chalkogenide, alkali metal chloride and alkaline earth metal chloride group, at least used a kind of metallic compound.In addition can organic substance and metal complex.
Form the formation method of above-mentioned each layer of light-emitting component, can enumerate resistance heating evaporation, electron beam evaporation plating, sputter, molecule layered manner or coating etc., be not particularly limited, under normal circumstances, consider from the viewpoint of element characteristic, preferably resistance heating evaporation or electron beam evaporation plating.
The thickness of organic layer, because the resistance value of luminescent substance is different, therefore can not limit, and is preferably 1～1000nm.The thickness of luminescent layer, electron transfer layer, hole transmission layer is preferably respectively below the above 200nm of 1nm, more preferably below the above 100nm of 5nm.
Organic coating layer of the present invention contains above-mentioned phosphinoxide.Realize the maximization of high-luminous-efficiency, color reproduction, the stacked thickness of organic coating layer that contains phosphinoxide can be 20nm～120nm, is preferably 40nm-80nm.In addition, consideration can realize the maximization of luminous efficiency, and further preferred organic overburden cover is 50nm～70nm.
The formation method of organic coating layer is not particularly limited, and can enumerate resistance heating evaporation, electron beam evaporation plating, sputter, molecule layered manner, coating, the black printing of spray, blade coating machine or laser transcription etc. and be not particularly limited.
Light-emitting component of the present invention has the function that can convert electrical energy into light.Here, electric energy mainly uses direct current, also can use pulse current or alternating current.Current value and magnitude of voltage are not particularly limited, and while considering the power consumption of element or life-span, the mode that should obtain maximum brightness with alap energy is selected.
Light-emitting component of the present invention can be preferably used as the display showing with for example matrix and/or sheet segmented mode.
Matrix-style refers to that pixel for showing, with two-dimensional arrangement such as grid-like or mosaic shapes, comes display text or image by the set of pixel.The shape of pixel, size can be determined according to purposes.For example, computer, watch-dog, television image and word use the length of side for the tetragonal pixel below 300um in showing conventionally, in addition, in the case of the such giant display of display floater, use the pixel that the length of side is mm grade.In the situation that monochrome shows, as long as arrange homochromy pixel, but in the situation that colour shows, red, green, blue color pixel is shown side by side.At this moment, representational have triangular form and stripe.And the driving method of this matrix can be to transmit line by line the simple structure that system drives, but considers that often active matrix excellence, therefore, all needs to use respectively according to purposes when operating characteristics.
Sheet segmented mode in the present invention is to form pattern in order to show predetermined information, makes by the luminous mode in the definite region of the configuration of this pattern.For example can enumerate: operating state demonstration and the Display panel of automobile etc. of the moment in digital clock or thermometer or temperature demonstration, stereo set or electromagnetic stove etc.And described matrix display and fragment demonstration also can coexist in same panel.
Light-emitting component of the present invention is preferably used as lighting source, can provide more slim and light than existing.
Brief description of the drawings
Fig. 1 is the index of refraction (n) of the specific wavelength of various organic materials.
Fig. 2 be various organic materials specific wavelength and attenuation coefficient (k) value.
Fig. 3 is the photoluminescence spectra of luminescent layer.
Fig. 4 is the luminous efficiency of BCP thickness and light-emitting component.
Fig. 5 is the colourity of BCP thickness and light-emitting component.
Fig. 6 is Ag, ITO, organic layer, the index of refraction (n) of Mg.
Fig. 7 is Ag, ITO, organic layer, the attenuation coefficient (k) of Mg.
Embodiment
In embodiment, use material for CuPc(copper peptide green grass or young crops), NPD(N, N'-diphenyl-N, N'-bis-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines), BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), compound (7) (phenyl two pyrenyl phosphine oxides), compound (16) (two (the diphenylphosphine oxygen base) anthracenes of 9,10-), Alq
3(three (oxine) aluminium), TBDB(4,4 '-bis-(N, N-xenyl) amino) biphenyl).
The manufacture method of film sample
Alkali-free glass substrate (Asahi Glass Co., Ltd, AN100) carry out the UV ozone washing processing of 20 minutes, and then be arranged in vacuum deposition apparatus, carry out exhaust, until the vacuum degree in device is than under the high vacuum degree condition of 1 × 10-3Pa, by resistance heating vapour deposition method, evaporation is prepared the film of about 1600nm.Evaporation rate is 1nm/s.
The film sample index of refraction of above-mentioned preparation and the assay method of attenuation coefficient are first to use reflection beam splitting film thickness gauge-FE3000( great Zhong Electronics Co., Ltd) measure the reflectivity of substrate normal, then, the light splitting reflectance spectrum obtaining is used to carat Mo-Ke Ruoni (K-K analysis3) conversion and applicableization of least square method, obtained index of refraction and the attenuation coefficient of the organic film of preparing on substrate.Shown in Fig. 1 and Fig. 2, use assay method of the present invention to obtain the index of refraction of the specific wavelength of the various organic materials of the embodiment of the present invention and comparative example (n) and attenuation coefficient (k) value.
Method of evaluating performance when organic coating layer material is used for light-emitting component
When above-mentioned various material is used for the cover layer of light-emitting component, use index of refraction and the attenuation coefficient of the above-mentioned various materials of obtaining, evaluated the performance (luminous efficiency and colourity ((CIE(y))) of light-emitting component.Evaluation method is to have used numerical method.In recent years, numerical method technical merit is developed by leaps and bounds, for example, The Journal of Chemical Physics, 63,1589 (1975), Journal of Applied Physics, 93,19 (2003) and Organic Electronics, 13,1386 (2012) introduce and there is very high experimental result and numerical result consistency.So described optical technology of the present invention aspect, has very high reliability.The numerical method (optical analog calculating) that the embodiment of the present invention has been used JP2006-277987 to record.Verify the correctness of above-mentioned numerical method result, preparation is with the light-emitting component of following preliminary experiment light-emitting component composition, and the results of property of this light-emitting component evaluation and the value that uses numerical method to calculate compare.
Preliminary experiment light-emitting component composition: glass substrate, ITO(116nm), CuPc(10nm), NPD(50nm) and, Alq
3(25nm), BCP, Li(0.5nm), Al(100nm) sequential cascade successively.Having prepared BCP is electric transmission layer material, and electron transfer layer is the light-emitting component to 6 kinds of thickness between 130nm at about 10nm, has evaluated performance.Fig. 4 and Fig. 5 are the experimental result of preliminary experiment and the contrast of numerical result.The luminous efficiency of the thickness of BCP shown in Fig. 4 and light-emitting component.The colourity of the thickness of BCP shown in Fig. 5 and light-emitting component.Experimental result and numerical result consistency are high, have confirmed to use this numerical method, realize correct experimental result.
Suppose that light-emitting component consists of Ag, ITO(50nm), organic layer (200nm), Mg(15nm), cover layer is sequential cascade successively.The photoluminescence spectra of luminescent layer has used Fig. 3 value.Ag, ITO, organic layer, index of refraction (n) and the attenuation coefficient (k) of Mg have used Fig. 6 and Fig. 7 value.
The evaluation method of thin film stability
Above-mentioned film sample, under atmosphere Atmosphere encloses, 25 DEG C, has kept 24 hours.Use reflection beam splitting film thickness gauge to measure index of refraction and the attenuation coefficient of the film sample of above-mentioned conservation condition front and back, evaluated rate of change.
Embodiment 1
Substrate (glass substrate), the first electrode (Ag/ITO(50nm)), organic layer (200nm), the second electrode (Mg(15nm)) and, organic coating layer (compound (the 7)) organic illuminating element of sequential cascade successively.
Organic illuminating element is evaluated.Evaluation result is in table 1.
Embodiment 2
Except organic coating layer material is compound (16), all the other are identical with embodiment 1.
Organic illuminating element is evaluated.Evaluation result is in table 1.
Comparative example 1
Except without organic coating layer, all the other are identical with embodiment 1.
Organic illuminating element is evaluated.Evaluation result is in table 1.
Comparative example 2
Except organic coating layer material is TBDB, all the other are identical with embodiment 1.
Organic illuminating element is evaluated.Evaluation result is in table 1.
Comparative example 3
Except organic coating layer material is Alq
3in addition, all the other are identical with embodiment 1.
Organic illuminating element is evaluated.Evaluation result is in table 1.
Table 1
Luminous efficiency (relative value) is that there is no the luminous efficiency of cover layer (comparative example 1) light-emitting component be the relative value of 100 o'clock.
Do not have the index of refraction of cover layer (comparative example 1) to be assumed to be air (1.00) value.
Embodiment 1 and embodiment 2 have obtained high-luminous-efficiency, and high color purity and thin film stability be satisfied result all.Comparative example 1 is the result that luminous efficiency is low.Comparative example 2 is to have obtained high-luminous-efficiency and high color purity, but thin film stability is poor, has caused crystallization.Comparative example 3 is compared with embodiment 2 with embodiment 1, and luminous efficiency is low.
Claims (7)
1. organic illuminating element, is characterized in that: substrate, and the first electrode, the luminescent layer that contains more than one organic tunics, sees through radiative the second electrode of aforementioned light emission layer, and the order successively of organic coating layer forms; Wherein, organic coating layer contains phosphinoxide.
2. organic illuminating element according to claim 1, is characterized in that: described phosphinoxide has following general formula (1):
Wherein, R
1～R
3can be identical or different, be selected from respectively hydrogen, halogen or without one or more in the alkyl, cycloalkyl, heterocyclic radical, alkenyl, cycloalkenyl group, alkynyl, alkoxyl, alkylthio group, aryl ether, aryl thioethers base, aryl, heteroaryl, amino or the silicyl that replace or replace, wherein R
1～R
3at least one is without the aryl or the heteroaryl that replace or replace, the integer that n is 1-4; Described substituting group is selected from the silicyl that aromatic heterocycle, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
3. organic illuminating element according to claim 2, is characterized in that: wherein, n is 1 or 2.
4. according to the organic illuminating element described in claim 2 or 3, it is characterized in that: R
1for aryl, substituted aryl, heteroaryl or substituted heteroaryl; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
5. organic illuminating element according to claim 4, is characterized in that: R
1for pyrenyl or replacement pyrenyl; It is 1-5 silicyl that described substituting group is selected from the alkyl of deuterium, halogen, C1-C15, the cycloalkyl of C2-C15, the heterocyclic radical of C3-C15, the alkenyl of C2-C15, the cycloalkenyl group of C4-C15, the alkynyl of C2-C15, the alkoxyl of C1-C55, the alkylthio group of C1-C55, the aryl ether of C6-C55, the aryl thioethers base of C6-C55, the aryl of C6-C55, heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of C5-C55.
6. organic illuminating element according to claim 4, is characterized in that: R
2, R
3in at least one is aryl, substituted aryl, heteroaryl or substituted heteroaryl; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
7. organic illuminating element according to claim 5, is characterized in that: R
2, R
3in at least one is aryl, substituted aryl, heteroaryl or substituted heteroaryl; Described substituting group is selected from the silicyl that heteroaryl, the amino of C1-C55 or the silicon atom number of C3-C15 of aryl, the C5-C55 of aryl thioethers base, the C6-C55 of aryl ether, the C6-C55 of alkylthio group, the C6-C55 of alkoxyl, the C1-C55 of alkynyl, the C1-C55 of cycloalkenyl group, the C2-C15 of alkenyl, the C4-C15 of heterocyclic radical, the C2-C15 of cycloalkyl, the C3-C15 of alkyl, the C2-C15 of deuterium, halogen, C1-C15 are 1-5.
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| CN201310052201.1A CN103996795A (en) | 2013-02-18 | 2013-02-18 | Organic luminous element |
| PCT/CN2014/072069 WO2014124599A1 (en) | 2013-02-18 | 2014-02-14 | Organic light-emitting element |
| TW103105268A TW201443198A (en) | 2013-02-18 | 2014-02-18 | Organic light-emitting element |
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|---|---|---|---|---|
| KR20160081105A (en) * | 2014-12-30 | 2016-07-08 | 삼성디스플레이 주식회사 | An organic light emitting device employing a layer for improving a light efficiency |
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| KR102285383B1 (en) * | 2014-09-12 | 2021-08-04 | 삼성디스플레이 주식회사 | Compounds for organic light-emitting device and organic light-emitting device comprising the same |
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| KR100700013B1 (en) * | 2004-11-26 | 2007-03-26 | 삼성에스디아이 주식회사 | Organic Electroluminescence Display Device and Fabricating Method of the same |
| JP5449742B2 (en) * | 2008-10-24 | 2014-03-19 | エルジー ディスプレイ カンパニー リミテッド | Organic EL device |
| JPWO2011043083A1 (en) * | 2009-10-09 | 2013-03-04 | 出光興産株式会社 | Organic electroluminescence device |
| KR102001263B1 (en) * | 2011-04-13 | 2019-07-17 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescence element |
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| KR20160081105A (en) * | 2014-12-30 | 2016-07-08 | 삼성디스플레이 주식회사 | An organic light emitting device employing a layer for improving a light efficiency |
| KR102396300B1 (en) * | 2014-12-30 | 2022-05-11 | 삼성디스플레이 주식회사 | An organic light emitting device employing a layer for improving a light efficiency |
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| TW201443198A (en) | 2014-11-16 |
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Application publication date: 20140820 |