WO2010001817A1 - 発光素子 - Google Patents
発光素子 Download PDFInfo
- Publication number
- WO2010001817A1 WO2010001817A1 PCT/JP2009/061674 JP2009061674W WO2010001817A1 WO 2010001817 A1 WO2010001817 A1 WO 2010001817A1 JP 2009061674 W JP2009061674 W JP 2009061674W WO 2010001817 A1 WO2010001817 A1 WO 2010001817A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- aryl
- heteroaryl
- light
- derivatives
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- -1 dibenzofuranyl groups Chemical group 0.000 claims abstract description 26
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000000732 arylene group Chemical group 0.000 claims abstract description 22
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000010409 thin film Substances 0.000 claims abstract description 21
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 20
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 16
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims abstract description 7
- 150000001454 anthracenes Chemical class 0.000 claims abstract description 5
- 150000003220 pyrenes Chemical class 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000005013 aryl ether group Chemical group 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 150000004832 aryl thioethers Chemical group 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 8
- 229910052709 silver Inorganic materials 0.000 claims description 8
- 239000004332 silver Substances 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims 2
- 238000005401 electroluminescence Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 98
- 230000032258 transport Effects 0.000 description 62
- 239000010408 film Substances 0.000 description 22
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 239000011521 glass Substances 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 150000004866 oxadiazoles Chemical class 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 0 **c1nc(c2ncc(*)nc2c2c3nc(*)c(*)n2)c3nc1* Chemical compound **c1nc(c2ncc(*)nc2c2c3nc(*)c(*)n2)c3nc1* 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 150000004826 dibenzofurans Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000004519 manufacturing process Methods 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
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- 125000005581 pyrene group Chemical group 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 3
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- JZXXUZWBECTQIC-UHFFFAOYSA-N [Li].C1=CC=CC2=NC(O)=CC=C21 Chemical compound [Li].C1=CC=CC2=NC(O)=CC=C21 JZXXUZWBECTQIC-UHFFFAOYSA-N 0.000 description 3
- 125000005577 anthracene group Chemical group 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 239000004305 biphenyl Substances 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 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
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 229910052710 silicon Inorganic materials 0.000 description 3
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- 238000004544 sputter deposition Methods 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-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
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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 2
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- 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 2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
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- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
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- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 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
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YPJRZWDWVBNDIW-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 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
- 230000036961 partial effect Effects 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 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
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 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
- 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 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 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
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/001—Pyrene dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Definitions
- the present invention relates to a pyrene compound or anthracene compound useful as a charge transport material, and a light emitting device using the same, and includes a display device, a flat panel display, a backlight, illumination, an interior, a sign, a signboard, an electrophotographic machine, and light
- the present invention relates to a light-emitting element that can be used in a field such as a signal generator.
- This light emitting element is characterized by thin light emission with high luminance under a low driving voltage and multicolor light emission by selecting a fluorescent material.
- organic thin-film light-emitting elements can be obtained in various light-emitting colors by using various fluorescent materials for the light-emitting layer, and therefore, research for practical application to displays and the like is active.
- the three primary color luminescent materials research on the green luminescent material is the most advanced, and at present, intensive research is being conducted to improve the characteristics of the red and blue luminescent materials.
- Organic thin-film light-emitting elements must satisfy improved luminous efficiency, lower drive voltage, and improved durability.
- improved luminous efficiency when the luminous efficiency is low, it is impossible to output an image that requires high luminance, and the amount of power consumed for outputting desired luminance increases.
- various luminescent materials have been developed (see, for example, Patent Documents 1 to 5).
- a technique of doping an alkali metal into a material used as an electron transport layer is disclosed (see Patent Documents 6 to 10).
- Patent Documents 6 to 10 are insufficient for achieving both low voltage driving and high luminous efficiency.
- An object of the present invention is to solve the problems of the prior art and to provide an organic thin film light emitting device that has both high luminous efficiency and low driving voltage.
- the present invention is an organic electroluminescent device comprising a thin film layer including at least a light emitting layer and an electron transport layer on a first electrode formed on a substrate, and a second electrode formed on the thin film layer,
- the electron transport layer includes an organic compound represented by the following general formula (1) and a donor compound.
- Y is either substituted or unsubstituted pyrene or substituted or unsubstituted anthracene.
- a 1 is selected from the group consisting of a single bond, an arylene group, and a heteroarylene group.
- Ar is a carbazolyl group, a dibenzofuranyl group. And selected from the group consisting of dibenzothiophenyl groups, which may be substituted or unsubstituted, n 1 is an integer of 1 to 3.
- an organic electroluminescent device that achieves both high luminous efficiency and low driving voltage.
- the light-emitting element of the present invention has a first electrode, a second electrode, and an organic layer interposed therebetween, and the organic layer includes at least a light-emitting layer, and the light-emitting layer emits light by electric energy.
- the organic layer is composed of only the light emitting layer, and 1) a hole transport layer / light emitting layer / electron transport layer, 2) a light emitting layer / electron transport layer, and 3) a hole transport layer / light emitting layer, etc.
- Each of the layers may be a single layer or a plurality of layers.
- the layers in contact with the electrodes may be referred to as a hole injection layer and an electron injection layer, respectively.
- the material is included in the hole transport material, and the electron injection material is included in the electron transport material.
- the electron transport layer in the light emitting device of the present invention contains a compound represented by the following general formula (1) and a donor compound.
- Y is either substituted or unsubstituted pyrene or substituted or unsubstituted anthracene.
- a 1 is selected from the group consisting of a single bond, an arylene group, and a heteroarylene group.
- Ar is selected from the group consisting of a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. These groups may be substituted or unsubstituted.
- n 1 is an integer of 1 to 3.
- the compound represented by the general formula (1) functions effectively as a light emitting material, particularly as a blue host material, as described in Patent Documents 1 to 5, for example. Function.
- the compound represented by the general formula (1) is used in combination with a specific donor compound, whereby both high luminous efficiency and low driving voltage can be achieved.
- an electron transport material it is necessary to efficiently transport electrons from the cathode, and it is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently.
- the material has a high electron affinity, a high electron mobility, excellent stability, and a substance that does not easily generate trapping impurities during manufacturing and use.
- a compound having a molecular weight of 400 or more that maintains a stable film quality is preferably used because a low molecular weight compound is likely to be crystallized to deteriorate the film quality.
- the compound represented by the general formula (1) is a compound that satisfies such a condition, and since it contains a pyrene or anthracene skeleton, it is excellent in electron transport property and electrochemical stability.
- a substituent selected from a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, which are bulky aromatic heterocyclic groups is introduced via an aryl group or a heteroaryl group, so that a pyrene or anthracene skeleton is formed.
- a stable film quality can be obtained while maintaining the high electron transport capability.
- the introduction of the substituent improves compatibility with the donor compound in a thin film state, and exhibits higher electron transport ability.
- the compound represented by the general formula (1) has a pyrene skeleton, the following compounds are preferable.
- R 1 to R 18 may be the same or different from each other, and may be hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether Selected from the group consisting of a group, an aryl group, a heteroaryl group, a halogen, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a silyl group, and —P ( ⁇ O) R 19 R 20 .
- R 19 and R 20 are an aryl group or a heteroaryl group.
- R 1 to R 20 may form a ring with adjacent substituents.
- n 2 is an integer of 1 to 3.
- X 2 is selected from the group consisting of —O—, —S— and —NR 21 —.
- R 21 is selected from the group consisting of hydrogen, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, and amino groups.
- R 21 may combine with R 11 or R 18 to form a ring.
- a 2 is selected from the group consisting of a single bond, an arylene group, and a heteroarylene group. Any two of R 1 to R 10 and any one of R 11 to R 21 are used for connection to A 2 . However, at least one of R 3 , R 6 and R 8 is a group different from R 1 .
- R 3 , R 6 , and R 8 are a group different from R 1 in the pyrene compound represented by the general formula (2), molecular symmetry is lowered, and a high-quality amorphous thin film can be formed. preferable.
- R 1 is an aryl group or a heteroaryl group, and at least one of A 2 is linked at the position of R 6 or R 8 .
- R 1 is an aryl group.
- R 2 is an alkyl group or a cycloalkyl group, and at least one of A 2 is connected at the position of R 6 or R 8 , whereby the amorphous nature of the molecule is improved and a stable thin film can be formed.
- a pyrene compound represented by the general formula (3) or (4) is preferable because of availability of raw materials or because synthesis is easy.
- R 30 to R 46 may be the same as or different from each other, and hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether Selected from the group consisting of a group, an aryl group, a heteroaryl group, a halogen, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a silyl group, and —P ( ⁇ O) R 47 R 48 .
- R 47 and R 48 are an aryl group or a heteroaryl group.
- R 30 to R 48 may form a ring with adjacent substituents.
- a 3 is an arylene group or a heteroarylene group.
- at least one of R 32 and R 34 is an aryl group or a heteroaryl group, or R 33 is an alkyl group or a cycloalkyl group.
- R 60 to R 75 may be the same or different and are each a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an aryl ether group, an arylthioether Selected from the group consisting of a group, an aryl group, a heteroaryl group, a halogen, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a silyl group, and —P ( ⁇ O) R 76 R 77 .
- R 76 and R 77 are an aryl group or a heteroaryl group.
- R 60 to R 77 may form a ring with adjacent substituents.
- a 4 is an arylene group or a heteroarylene group.
- at least one of R 62 and R 64 is an aryl group or a heteroaryl group, or R 63 is an alkyl group or a cycloalkyl group.
- At least one of R 11 to R 18 in the general formula (2) or at least one of R 39 to R 46 in the general formula (3) is selected from an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.
- Preferred examples include that the group is selected, R 62 and R 64 in the general formula (4) are hydrogen, R 63 is an alkyl group, and R 67 is an aryl group or a heteroaryl group. It is done.
- at least two adjacent members out of R 11 to R 18 or at least two adjacent members out of R 39 to R 46 may be combined to form a ring. Such a structure is preferable because the interaction between pyrene compounds is suppressed, high luminous efficiency is possible, and thin film stability is also improved.
- R 80 to R 97 may be the same or different and are each hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an aryl ether group.
- R 98 and R 99 are an aryl group or a heteroaryl group.
- R 80 to R 99 may form a ring with adjacent substituents.
- n 5 is an integer of 1 to 2.
- X 5 is selected from the group consisting of —O—, —S— and —NR 100 —.
- R 100 is selected from the group consisting of hydrogen, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, and amino groups.
- R 100 may combine with R 90 or R 97 to form a ring.
- a 5 is selected from the group consisting of a single bond, an arylene group, and a heteroarylene group. Any five of R 80 to R 89 and any one of R 90 to R 100 are used for connection with A 5 .
- R 90 to R 97 in the general formula (5) is at least one selected from hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, a phenyl group, a naphthyl group, and a heteroaryl group
- the thin film stability thus, a light emitting element with high luminous efficiency and high luminous efficiency can be realized.
- an anthracene compound represented by the general formula (6) or (7) is preferable because of availability of raw materials or easy synthesis.
- R 110 to R 126 may be the same or different and are each hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, phenyl group, or alkyl-substituted.
- Phenyl group alkoxy substituted phenyl group, aryl substituted phenyl group, naphthyl group, alkyl substituted naphthyl group, alkoxy substituted naphthyl group, aryl substituted naphthyl group, phenanthryl group, alkyl substituted phenanthryl group, alkoxy substituted phenanthryl group, aryl substituted phenanthryl group, hetero Selected from aryl group and silyl group.
- a 6 is a heteroarylene group or an arylene group having 6 to 12 carbon atoms.
- R 140 to R 148 may be the same or different and are each hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an aryl ether group.
- R 156 and R 157 are an aryl group or a heteroaryl group.
- R 149 to R 155 may be the same or different and are selected from hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, a phenyl group, a naphthyl group, and a heteroaryl group.
- a 7 is selected from a single bond, an arylene group, and a heteroarylene group.
- R 114 in the general formula (6) or R 144 in the general formula (7) is hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkoxy group, alkylthio group, aryl group, heteroaryl group, amino group, silyl group.
- a preferred form is selected from the group consisting of a ring structure formed between a group and an adjacent substituent. Such a structure is preferable because the interaction between anthracene compounds is suppressed, high luminous efficiency is possible, and thin film stability is improved.
- the alkyl group is, for example, a saturated aliphatic carbonization such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group.
- a hydrogen group is shown, which may or may not have a substituent.
- an alkyl group, an aryl group, heteroaryl group etc. can be mentioned, This point is common also in the following description.
- the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 and more preferably 1 to 8 from the viewpoint of availability and cost.
- the cycloalkyl group represents, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may or may not have a substituent.
- carbon number of an alkyl group part is not specifically limited, Usually, it is the range of 3-20.
- the heterocyclic group refers to an aliphatic ring having atoms other than carbon, such as a pyran ring, a piperidine ring, and a cyclic amide, in the ring, which may or may not have a substituent. .
- carbon number of a heterocyclic group is not specifically limited, Usually, it is the range of 2-20.
- alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, which may or may not have a substituent.
- the number of carbon atoms of the alkenyl group is not particularly limited, but is usually in the range of 2-20.
- the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may have a substituent. You don't have to.
- the alkynyl group indicates, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may or may not have a substituent.
- the number of carbon atoms of the alkynyl group is not particularly limited, but is usually in the range of 2-20.
- the alkoxy group refers to, for example, a functional group having an aliphatic hydrocarbon group bonded through an ether bond such as a methoxy group, an ethoxy group, or a propoxy group, and the aliphatic hydrocarbon group may have a substituent. It may not have. Although carbon number of an alkoxy group is not specifically limited, Usually, it is the range of 1-20.
- the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
- the hydrocarbon group of the alkylthio group may or may not have a substituent. Although carbon number of an alkylthio group is not specifically limited, Usually, it is the range of 1-20.
- An aryl ether group refers to a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have a substituent. Good. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.
- the aryl thioether group is a group in which an oxygen atom of an ether bond of an aryl ether group is substituted with a sulfur atom.
- the aromatic hydrocarbon group in the aryl ether group may or may not have a substituent. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.
- An aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, or a terphenyl group.
- the aryl group may or may not have a substituent.
- the number of carbon atoms of the aryl group is not particularly limited, but is usually in the range of 6 to 40.
- a heteroaryl group is a cyclic aromatic group having one or more atoms other than carbon, such as a pyridyl group, a quinolinyl group, a pyrazinyl group, a naphthyridyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group. This can be unsubstituted or substituted.
- the number of carbon atoms of the heteroaryl group is not particularly limited, but is usually in the range of 2 to 30.
- the connecting position of the heteroaryl group may be any part. For example, in the case of a pyridyl group, it may be any of 2-pyridyl group, 3-pyridyl group and 4-pyridyl group.
- the halogen atom means fluorine, chlorine, bromine or iodine.
- the carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, and phosphine oxide group may or may not have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, and an aryl group. Group, heteroaryl group and the like, and these substituents may be further substituted.
- the silyl group refers to, for example, a functional group having a bond to a silicon atom such as a trimethylsilyl group, which may or may not have a substituent.
- the carbon number of the silyl group is not particularly limited, but is usually in the range of 3-20.
- the number of silicon is usually 1-6.
- An arylene group refers to a divalent group derived from an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, or a terphenyl group, which has a substituent. It does not have to be.
- the number of carbon atoms of the arylene group is not particularly limited, but is usually in the range of 6 to 40.
- a in the general formula (1) is an arylene group, the arylene group may or may not have a substituent, but the carbon number including the substituent is in the range of 6 to 30.
- a heteroarylene group is a cyclic aromatic group having one or more atoms other than carbon, such as a pyridyl group, a quinolinyl group, a pyrazinyl group, a naphthyridyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group.
- a divalent group to be derived is shown, which may or may not have a substituent.
- the number of carbon atoms of the heteroarylene group is not particularly limited, but is usually in the range of 2 to 30 including the substituent.
- any adjacent two substituents (for example, R 1 and R 2 in formula (1)) can be bonded to each other to form a conjugated or non-conjugated condensed ring.
- a constituent element of the condensed ring in addition to carbon, nitrogen, oxygen, sulfur, phosphorus and silicon atoms may be contained, or further condensed with another ring.
- said organic compound Specifically, the following examples are mentioned.
- the first electrode and the second electrode have a role of supplying a sufficient current for light emission of the device, and at least one of them is transparent or translucent to extract light. It is desirable.
- the first electrode formed on the substrate is a transparent electrode, which is an anode, and the second electrode is a cathode.
- the material used for the first electrode may be tin oxide, indium oxide, indium tin oxide (ITO), zinc indium oxide (ITO), as long as the material can efficiently inject holes into the organic layer and is transparent or translucent to extract light.
- IZO tin oxide
- ITO indium tin oxide
- ITO zinc indium oxide
- IZO conductive metal oxides
- metals such as gold, silver and chromium
- inorganic conductive materials such as copper iodide and copper sulfide
- conductive polymers such as polythiophene, polypyrrole and polyaniline
- ITO glass or Nesa glass it is particularly desirable to use ITO glass or Nesa glass.
- the resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the element can be supplied, but it is desirable that the resistance be low from the viewpoint of power consumption of the element.
- an ITO substrate with a resistance of 300 ⁇ / ⁇ or less will function as a device electrode, but since it is now possible to supply a substrate with a resistance of approximately 10 ⁇ / ⁇ , use a substrate with a low resistance of 20 ⁇ / ⁇ or less. Is particularly desirable.
- the thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.
- the light emitting element is preferably formed over a substrate.
- a glass substrate such as soda glass or non-alkali glass is preferably used.
- the thickness of the glass substrate it is sufficient that the thickness is sufficient to maintain the mechanical strength.
- alkali-free glass is preferred because it is better that there are fewer ions eluted from the glass.
- soda lime glass provided with a barrier coat such as SiO 2 is also commercially available and can be used.
- the substrate need not be glass, and for example, an anode may be formed on a plastic substrate.
- the ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, and a chemical reaction method.
- the material used for the second electrode is not particularly limited as long as it can efficiently inject electrons into the light emitting layer.
- metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys and multilayer stacks of these metals with low work function metals such as lithium, sodium, potassium, calcium, and magnesium Is preferred.
- aluminum, silver, and magnesium are preferable as the main component from the viewpoints of electrical resistance, ease of film formation, film stability, luminous efficiency, and the like.
- magnesium and silver are preferable because electron injection into the electron transport layer and the electron injection layer in the present invention is facilitated and low voltage driving is possible.
- metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, poly
- an organic polymer compound such as vinyl chloride or a hydrocarbon polymer compound is laminated on the second electrode as a protective film layer.
- the protective film layer is selected from a material that transmits light in the visible light region.
- the production method of these electrodes is not particularly limited, such as resistance heating, electron beam, sputtering, ion plating and coating.
- the hole transport layer is formed by a method of laminating or mixing one or more hole transport materials or a method using a mixture of a hole transport material and a polymer binder.
- the hole transport layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole transport material.
- the hole transport material needs to efficiently transport holes from the positive electrode between electrodes to which an electric field is applied, and has a high hole injection efficiency, and it is desirable to transport the injected holes efficiently. For this purpose, it is required that the material has an appropriate ionization potential, has a high hole mobility, is excellent in stability, and does not easily generate trapping impurities during manufacture and use.
- the substance satisfying such conditions is not particularly limited, but 4,4′-bis (N- (3-methylphenyl) -N-phenylamino) biphenyl, 4,4′-bis (N— Triphenylamine derivatives such as (1-naphthyl) -N-phenylamino) biphenyl, 4,4 ′, 4 ′′ -tris (3-methylphenyl (phenyl) amino) triphenylamine, bis (N-allylcarbazole) or Biscarbazole derivatives such as bis (N-alkylcarbazole), pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives and other heterocyclic compounds, fullerene derivatives, polymers
- the polycarbonate having the monomer in the side chain Chromatography with or styrene derivatives, polythiophene, poly(
- inorganic compounds such as p-type Si and p-type SiC can also be used.
- a compound represented by the following general formula (8), tetrafluorotetracyanoquinodimethane (4F-TCNQ), or molybdenum oxide can also be used.
- R 170 to R 175 may be the same or different and are selected from the group consisting of halogen, sulfonyl group, carbonyl group, nitro group, cyano group, and trifluoromethyl group.
- the compound (9) (1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile
- the hole transport layer or the hole injection layer the hole transport layer adjacent to the light emitting layer.
- the energy barrier between the layers is relaxed, and a lower voltage drive is preferable.
- the light emitting layer may be either a single layer or a plurality of layers, each formed of a light emitting material (host material, dopant material), which may be a mixture of a host material and a dopant material or a host material alone. It may be either. That is, in the light emitting element of the present invention, only the host material or the dopant material may emit light in each light emitting layer, or both the host material and the dopant material may emit light. From the viewpoint of efficiently using electric energy and obtaining light emission with high color purity, the light emitting layer is preferably a mixture of a host material and a dopant material. Further, the host material and the dopant material may be either one kind or a plurality of combinations, respectively.
- a light emitting material host material, dopant material
- the dopant material may be included in the entire host material or may be partially included.
- the dopant material may be laminated or dispersed.
- the dopant material can control the emission color. If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, so that it is preferably used at 20% by weight or less, more preferably 10% by weight or less with respect to the host material.
- the doping method can be formed by a co-evaporation method with a host material, but may be simultaneously deposited after being previously mixed with the host material.
- the light-emitting material includes condensed ring derivatives such as anthracene and pyrene, which have been known as light emitters, metal chelated oxinoid compounds such as tris (8-quinolinolato) aluminum, bisstyrylanthracene derivatives and diesters.
- condensed ring derivatives such as anthracene and pyrene, which have been known as light emitters
- metal chelated oxinoid compounds such as tris (8-quinolinolato) aluminum, bisstyrylanthracene derivatives and diesters.
- Bisstyryl derivatives such as styrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, dibenzofuran derivatives, carbazole
- polyphenylene vinylene derivatives, polyparaphenylene derivatives, polythiophene derivatives, etc. can be used, but are not particularly limited. Not shall.
- the host material contained in the light emitting material is not particularly limited, but is a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene, and derivatives thereof, N, Aromatic amine derivatives such as N′-dinaphthyl-N, N′-diphenyl-4,4′-diphenyl-1,1′-diamine, metal chelating oxinoids including tris (8-quinolinato) aluminum (III) Compounds, bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, pyr
- the host used when the light emitting layer emits phosphorescence includes metal chelated oxinoid compounds, chrysene derivatives, binaphthyl derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivatives, carboline derivatives, pyridoindole derivatives, triazines. Derivatives and the like are preferably used.
- the dopant material is not particularly limited, but a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, triphenylene, perylene, fluoranthene, fluorene, indene or a derivative thereof (for example, 2- (benzothiazol-2-yl) ) -9,10-diphenylanthracene and 5,6,11,12-tetraphenylnaphthacene), furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, Compounds having heteroaryl rings such as benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, qui
- the dopant used when the light emitting layer emits phosphorescence includes iridium (Ir), ruthenium (Ru), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re). It is preferably a metal complex compound containing at least one metal selected from the group, and the ligand preferably has a nitrogen-containing aromatic heterocycle such as a phenylpyridine skeleton or a phenylquinoline skeleton. However, it is not limited to these, and an appropriate complex is selected from the relationship with the required emission color, device performance, and host compound.
- the compounds represented by the general formulas (1) to (7) are used in the electron transport layer as in the present invention, it is excellent in that the phosphorescent material is included in the light emitting layer among the above. It is preferable because high emission efficiency can be achieved by injection characteristics and electron transport characteristics.
- Preferable combinations of phosphorescent materials include, for example, combinations of the above metal chelated oxinoid compounds, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivatives, carboline derivatives, pyridoindole derivatives, triazine derivatives, and the like.
- the metal contained in the metal chelated oxinoid compound is preferably iridium, palladium, platinum or the like, with iridium being particularly preferred.
- Preferred phosphorescent host or dopant is not particularly limited, but specific examples include the following.
- the electron transport layer is a layer in which electrons are injected from the cathode and further transports electrons.
- the electron transport layer has high electron injection efficiency, and it is desired to efficiently transport injected electrons. Therefore, it is desirable that the electron transport layer is made of a material having a high electron affinity, a high electron mobility, excellent stability, and a trapping impurity that is unlikely to be generated during manufacture and use.
- the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
- the compounds represented by the general formulas (1) to (7) are compounds satisfying the above conditions, and are preferably used as an electron transporting material because of their high electron injecting and transporting ability.
- the compounds represented by the general formulas (1) to (7) contain a pyrene skeleton and a specific substituent, they have excellent electron injection / transport properties and electrochemical stability.
- the introduction of the substituent improves compatibility in a thin film state with a donor compound described later, and exhibits higher electron injecting and transporting ability.
- the transport of electrons from the cathode to the light emitting layer is promoted, and both high luminous efficiency and low driving voltage can be achieved.
- the compounds represented by the general formulas (1) to (7) of the present invention have a substituent containing a heteroaryl ring structure having an electron-accepting nitrogen, the electron injection or electron transport ability from the cathode Are preferably used.
- This substituent is preferably bonded to pyrene or anthracene directly or via a linking group.
- the electron-accepting nitrogen in the present invention represents a nitrogen atom that forms a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron accepting property. Therefore, the heteroaryl ring containing electron-accepting nitrogen has high electron affinity and excellent electron transporting ability. By using a material having this for the electron transporting layer, the driving voltage of the light-emitting element can be reduced.
- Heteroaryl rings containing electron-accepting nitrogen include, for example, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, oxalate ring, Examples include a diazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthrimidazole ring.
- compounds represented by the general formulas (1) to (7) having a 6-membered ring structure such as a pyridine ring, a pyrimidine ring, and a triazine ring are preferable, and a compound having a pyridine ring is more preferable.
- the pyridine rings it is more preferable that the 3-pyridyl group is directly bonded to pyrene or anthracene because the electron injection or electron transport capability is the highest and the driving voltage is low.
- the linking group is preferably an arylene group or a heteroarylene group, and these are substituted with an alkyl group. May be.
- an arylene group or heteroarylene group having 3 to 12 carbon atoms including a substituent is preferable, and a phenylene group is particularly preferable.
- the electron transport material used in the present invention need not be limited to each of the compounds represented by the general formulas (1) to (7) of the present invention.
- One or more electron transport materials may be mixed with the compound of the present invention as long as the effects of the present invention are not impaired.
- the electron transport material that can be mixed is not particularly limited, but is a compound having a condensed aryl ring such as naphthalene, anthracene, or pyrene or a derivative thereof, or a styryl-based fragrance represented by 4,4′-bis (diphenylethenyl) biphenyl.
- Ring derivatives perylene derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives, quinolinol complexes such as tris (8-quinolinolato) aluminum (III) and hydroxy Hydroxazole complexes such as phenyloxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes can be mentioned. It is preferable to use a compound containing a reel ring structure.
- Examples of these compounds having a heteroaryl ring structure include benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, phenanthroline.
- Preferred examples include derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives, and naphthyridine derivatives.
- imidazole derivatives such as tris (N-phenylbenzimidazol-2-yl) benzene, oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) 1,3,4-oxadiazolyl] phenylene, Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine and 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,2 ′
- a benzoquinoline derivative such as bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, 2,5-bis (6 ′-(2 ′, 2 ′′ -bipyridyl))-1, Bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilole, 1,3-bis (4 ′-(2,2 )
- the donor compound in the present invention is a compound that facilitates electron injection from the second electrode or the electron injection layer to the electron transport layer by improving the electron injection barrier, and further improves the electrical conductivity of the electron transport layer. That is, the light-emitting device of the present invention is obtained by doping an electron transport layer with a donor compound in order to improve the electron transport capability.
- Preferred examples of the donor compound in the present invention include an alkali metal, an inorganic salt containing an alkali metal, a complex of an alkali metal and an organic substance, an alkaline earth metal, an inorganic salt containing an alkaline earth metal, or an alkaline earth metal. And a complex of organic substance.
- alkali metals and alkaline earth metals include alkali metals such as lithium, sodium and cesium, which have a low work function and a large effect of improving the electron transport ability, and alkaline earth metals such as magnesium and calcium.
- inorganic salts include oxides such as LiO and Li 2 O, nitrides, fluorides such as LiF, NaF, and KF, Li 2 CO 3 , Na 2 CO 3 , K 2 CO 3 , Rb 2 CO 3 , Examples thereof include carbonates such as Cs 2 CO 3 .
- a preferable example of the alkali metal or alkaline earth metal is lithium from the viewpoint that the raw materials are inexpensive and easy to synthesize.
- Preferred examples of the organic substance in the complex with the organic substance include quinolinol, benzoquinolinol, flavonol, hydroxyimidazopyridine, hydroxybenzazole, hydroxytriazole and the like.
- a complex of an alkali metal and an organic substance is preferable, and a complex of lithium and an organic substance is more preferable.
- a complex of lithium and a compound having a heteroaryl ring containing electron-accepting nitrogen is preferable, and lithium quinolinol is particularly preferable.
- the doping ratio of the donor compound in the electron transport layer when the doping ratio of the donor compound in the electron transport layer is appropriate, the injection ratio of electrons from the cathode or the electron injection layer to the electron transport layer increases, and the cathode and the electron injection layer or the electron injection layer and the electron The energy barrier between the transport layers is reduced and the driving voltage is reduced.
- the suitable doping concentration varies depending on the material and the film thickness of the doping region, but the molar ratio of the organic compound to the donor compound is preferably in the range of 100: 1 to 1: 100, more preferably 10: 1 to 1:10.
- the method of improving the electron transport ability by doping a donor compound in the electron transport layer is particularly effective when the thin film layer is thick. It is particularly preferably used when the total film thickness of the electron transport layer and the light emitting layer is 50 nm or more.
- the total film thickness of the electron transport layer and the light emitting layer is 50 nm or more.
- the total film thickness of the electron transport layer and the light-emitting layer is 50 nm or more, and in the case of long-wavelength light emission such as red, it may be a thick film near 100 nm. .
- the film thickness of the electron transport layer to be doped may be a part or all of the electron transport layer, but the thicker the entire electron transport layer, the better the doping concentration.
- the light emitting layer is doped with the donor compound, it is desirable to provide a non-doped region at the light emitting layer / electron transport layer interface when it adversely affects the light emission efficiency.
- each layer constituting the light emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, etc., but resistance heating vapor deposition or electron beam vapor deposition is usually used in terms of element characteristics. preferable.
- the thickness of the organic layer is not limited because it depends on the resistance value of the luminescent material, but is preferably 1 to 1000 nm.
- the film thicknesses of the light emitting layer, the electron transport layer, and the hole transport layer are each preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.
- the light emitting element of the present invention has a function of converting electrical energy into light.
- a direct current is mainly used as the electric energy, but a pulse current or an alternating current can also be used.
- the current value and voltage value are not particularly limited, but should be selected so that the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the device.
- the light-emitting element of the present invention is suitably used as a display for displaying in a matrix and / or segment system, for example.
- pixels for display are arranged two-dimensionally such as a lattice shape or a mosaic shape, and characters and images are displayed by a set of pixels.
- the shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 ⁇ m or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become.
- monochrome display pixels of the same color may be arranged, but in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type.
- the matrix driving method may be either a line sequential driving method or an active matrix. Although the structure of the line sequential drive is simple, the active matrix may be superior in consideration of the operation characteristics, and it is necessary to use it depending on the application.
- the segment system in the present invention is a system in which a pattern is formed so as to display predetermined information and an area determined by the arrangement of the pattern is caused to emit light.
- a pattern is formed so as to display predetermined information and an area determined by the arrangement of the pattern is caused to emit light.
- the time and temperature display in a digital clock or a thermometer can be mentioned.
- the matrix display and the segment display may coexist in the same panel.
- the light emitting device of the present invention is also preferably used as a backlight for various devices.
- the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like.
- the light-emitting element of the present invention is preferably used for a backlight for a liquid crystal display device, particularly a personal computer for which a reduction in thickness is being considered, and a backlight that is thinner and lighter than conventional ones can be provided.
- Example 1 A glass substrate (manufactured by Geomat Co., Ltd., 11 ⁇ / ⁇ , sputtered product) having an ITO transparent conductive film deposited to 150 nm was cut into 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semico Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 ⁇ 4 Pa or less.
- “Semico Clean 56” trade name, manufactured by Furuuchi Chemical Co., Ltd.
- the film thickness referred to here is a crystal oscillation type film thickness monitor display value.
- Examples 2-32 A light emitting device was produced in the same manner as in Example 1 except that the materials described in Tables 1 and 2 were used as the host material, the dopant material, and the electron transport layer. The results of each example are shown in Tables 1 and 2.
- Comparative Example 1 A light emitting device was fabricated in the same manner as in Example 1 except that no donor compound was used as the electron transport layer. When this light emitting device was DC-driven at 10 mA / cm 2 , high-efficiency blue light emission with a driving voltage of 6.4 V and an external quantum efficiency of 4.2% was obtained.
- Comparative Examples 2-8 A light emitting device was fabricated in the same manner as in Example 1 except that the materials listed in Tables 1 and 2 were used as the host material, dopant material, and electron transport material. The results of each comparative example are shown in Tables 1 and 2.
- Example 33 A glass substrate (manufactured by Geomat Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which ITO transparent conductive film was deposited at 165 nm was cut into 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semico Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 ⁇ 4 Pa or less.
- “Semico Clean 56” trade name, manufactured by Furuuchi Chemical Co., Ltd.
- 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile is used as a hole injecting material by a resistance heating method, 10 nm, and 4,4′-bis (N- (1 -Naphthyl) -N-phenylamino) biphenyl was evaporated to 50 nm.
- a compound (H-1) as a host material and a compound (D-2) as a dopant material were vapor-deposited on the light emitting material to a thickness of 40 nm so as to have a doping concentration of 5%.
- the film thickness referred to here is a crystal oscillation type film thickness monitor display value.
- Examples 34-102 A light emitting device was produced in the same manner as in Example 33 except that the materials described in Tables 3 to 6 were used as the host material, the dopant material, and the electron transport layer. The results of each example are shown in Tables 3-6.
- Comparative Examples 9-16 A light emitting device was fabricated in the same manner as in Example 33 except that the materials described in Tables 3 to 6 were used as the host material, the dopant material, and the electron transport material. The results of each comparative example are shown in Tables 3-6.
- the light emitting device material of the present invention can be used for a light emitting device or the like, and can provide a light emitting device material having excellent thin film stability. According to the present invention, a light emitting device having both high luminous efficiency and low driving voltage can be obtained.
- the light-emitting element of the present invention can be used in the fields of display elements, flat panel displays, backlights, illumination, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like.
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Abstract
Description
本発明の発光素子は、各種機器等のバックライトとしても好ましく用いられる。バックライトは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ装置、自動車パネル、表示板および標識などに使用される。特に、液晶表示装置、中でも薄型化が検討されているパソコン用途のバックライトに本発明の発光素子は好ましく用いられ、従来のものより薄型で軽量なバックライトを提供できる。
ITO透明導電膜を150nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、銅フタロシアニンを10nm、正孔輸送材料として、4,4’-ビス(N-(1-ナフチル)-N-フェニルアミノ)ビフェニルを50nm蒸着した。次に、発光材料に、ホスト材料として化合物(H-1)を、ドーパント材料として化合物(D-1)をドープ濃度が5重量%になるようにして40nmの厚さに蒸着した。次に、有機化合物(1E-1)とドナー性化合物(フッ化リチウム)を混合した層を、電子輸送層として蒸着速度比1:1(=0.05nm/s:0.05nm/s)で20nmの厚さに蒸着して積層した。
ホスト材料、ドーパント材料、電子輸送層として表1~2に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。各実施例の結果は表1~2に示した。
電子輸送層としてドナー性化合物を用いなかったこと以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、駆動電圧6.4V、外部量子効率4.2%の高効率青色発光が得られた。
ホスト材料、ドーパント材料、電子輸送材料として表1~2に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。各比較例の結果は表1~2に示した。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、1,4,5,8,9,12-ヘキサアザトリフェニレンヘキサカルボニトリルを10nm、正孔輸送材料として、4,4’-ビス(N-(1-ナフチル)-N-フェニルアミノ)ビフェニルを50nm蒸着した。次に、発光材料に、ホスト材料として化合物(H-1)を、ドーパント材料として化合物(D-2)をドープ濃度が5%になるようにして40nmの厚さに蒸着した。次に、有機化合物(1E-1)とドナー性化合物(リチウムキノリノール)を蒸着速度比1:1(=0.05nm/s:0.05nm/s)で混合した層を、電子輸送層として10nmの厚さに積層した。
ホスト材料、ドーパント材料、電子輸送層として表3~6に記載した材料を用いた以外は、実施例33と同様にして発光素子を作製した。各実施例の結果は表3~6に示した。
ホスト材料、ドーパント材料、電子輸送材料として表3~6に記載した材料を用いた以外は、実施例33と同様にして発光素子を作製した。各比較例の結果は表3~6に示した。
Claims (13)
- ドナー性化合物がアルカリ金属、アルカリ金属を含有する無機塩、アルカリ金属と有機物との錯体、アルカリ土類金属、アルカリ土類金属を含有する無機塩またはアルカリ土類金属と有機物との錯体であることを特徴とする請求項1記載の発光素子。
- ドナー性化合物がアルカリ金属と有機物との錯体またはアルカリ土類金属と有機物との錯体であることを特徴とする請求項1または2記載の発光素子。
- 発光層がりん光発光材料を含有することを特徴とする1~3のいずれか記載の発光素子。
- 前記有機化合物が下記一般式(2)で表されることを特徴とする請求項1~5のいずれか記載の発光素子。
- 前記有機化合物が下記一般式(3)で表されることを特徴とする請求項6記載の発光素子。
- 前記有機化合物が下記一般式(4)で表されることを特徴とする請求項6記載の発光素子。
- 前記有機化合物が下記一般式(5)で表されることを特徴とする請求項1~5のいずれか記載の発光素子。
- 前記有機化合物が下記一般式(6)で表されることを特徴とする請求項9記載の発光素子。
- 前記有機化合物が下記一般式(7)で表されることを特徴とする請求項9記載の発光素子。
- 前記有機化合物中のピレンまたはアントラセンが、電子受容性窒素を有するヘテロアリール環構造を含む置換基を有することを特徴とする請求項1~11のいずれか記載の発光素子。
- 第二電極がマグネシウムと銀で構成されることを特徴とする請求項1~12のいずれか記載の発光素子。
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EP2296204B1 (en) | 2018-01-31 |
JP5565494B2 (ja) | 2014-08-06 |
CN102084514A (zh) | 2011-06-01 |
TW201009045A (en) | 2010-03-01 |
TWI601803B (zh) | 2017-10-11 |
EP2296204A1 (en) | 2011-03-16 |
US8502201B2 (en) | 2013-08-06 |
KR20110040874A (ko) | 2011-04-20 |
JP5299288B2 (ja) | 2013-09-25 |
JP2013179320A (ja) | 2013-09-09 |
EP2296204A4 (en) | 2011-07-27 |
US20110121268A1 (en) | 2011-05-26 |
JPWO2010001817A1 (ja) | 2011-12-22 |
KR101668887B1 (ko) | 2016-10-24 |
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