TW201700457A - 複數種主體材料及包括其之有機電致發光裝置 - Google Patents
複數種主體材料及包括其之有機電致發光裝置 Download PDFInfo
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- TW201700457A TW201700457A TW105115849A TW105115849A TW201700457A TW 201700457 A TW201700457 A TW 201700457A TW 105115849 A TW105115849 A TW 105115849A TW 105115849 A TW105115849 A TW 105115849A TW 201700457 A TW201700457 A TW 201700457A
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- substituted
- unsubstituted
- group
- aryl
- alkyl
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- 239000000463 material Substances 0.000 title description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 239000002019 doping agent Substances 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 20
- -1 cyano, carboxy Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 238000005401 electroluminescence Methods 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005266 diarylamine group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 86
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 230000001976 improved effect Effects 0.000 description 7
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 125000002971 oxazolyl group Chemical group 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000005286 illumination Methods 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- 101100451713 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) HTL1 gene Proteins 0.000 description 1
- 229910003564 SiAlON 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
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 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 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 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
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 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
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
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Abstract
本發明係關於一種有機電致發光裝置,其包括至少一個安置於陽極與陰極之間的發光層,其中所述發光層包括主體及磷光摻雜劑,其中所述主體包括複數種主體化合物,其中所述複數種主體化合物中之至少第一主體化合物具有經萘基-苯基及芳基取代之胺-咔唑結構,且第二主體化合物具有包括含氮雜芳基之二-C-苯并咔唑結構。與使用唯一主體化合物之習知有機電致發光裝置相比,藉由使用本發明之所述複數種主體化合物,所述有機電致發光裝置可具有長久壽命,同時在高照度下維持高效率。
Description
本發明係關於複數種主體材料及包括其之有機電致發光裝置。
電致發光(EL)裝置為自身發光裝置,其優點在於其提供較寬視角、較高對比率及較快回應時間。有機EL裝置由伊士曼柯達(Eastman Kodak)藉由使用小芳族二胺分子及鋁錯合物作為形成發光層之材料而首先研發[《應用物理學快報(Appl.Phys.Lett.)》51,913,1987]。
在有機電致發光裝置(OLED)中,將電施加至有機發光材料,所述有機發光材料將電能轉化成光。一般而言,OLED具有包括陽極、陰極及安置於兩個電極之間的有機層之結構。OLED之有機層可包括電洞注入層、電洞傳輸層、電子阻擋層、發光層(包括主體材料及摻雜材料)、電子緩衝層、電洞阻擋層、電子傳輸層、電子注入層等。製備有機層之材料可根據其功能分類為電洞注入材料、電洞傳輸材料、電子阻擋材料、發光材料、電子緩衝材料、電洞阻擋材料、電子傳輸材料、電子注入材料等。電洞及電子藉由將電施加
至OLED分別自陽極及陰極注入至發光層;具有高能量之激子藉由電洞及電子之重組形成,其使有機發光化合物處於激發態,且發光化合物之激發態返回至基態,此將能量轉化成光,且導致光發射。
決定OLED之發光效率之最重要的因素為發光材料。發光材料需要具有高量子效率、高電子遷移率及高電洞遷移率。此外,由發光材料形成之發光層需要為均勻且穩定的。根據利用光發射觀測之顏色,發光材料可歸類為發射藍光、發射綠光或發射紅光之材料,且其中可另外包含發射黃光或發射橙光之材料。此外,發光材料可根據其功能歸類為主體材料及摻雜材料。近來,迫切需要開發提供高效率及長久壽命之OLED。特定言之,考慮針對中尺寸或大尺寸OLED板之EL要求,必須迫切地開發展示比習知材料好之效能之材料。為了實現開發,作為溶劑在固態及能量載體中起作用之主體材料應具有高純度及適當之分子量以在真空中沈積。另外,主體材料應具有高玻璃轉化溫度及高熱分解溫度以確保熱穩定性;高電化學穩定性以具有長久壽命;易於製備非晶形薄膜;以及對鄰近層材料之良好黏著性。此外,主體材料不應移動至鄰近層。
發光材料可藉由將主體與摻雜劑組合來製備以改進色彩純度、發光效率及穩定性。一般而言,展示良好EL效能之裝置包括藉由將摻雜劑摻雜至主體來製備之發光層。主體材料在使用主體/摻雜劑系統時極大地影響EL裝置之效率及壽命,且因此其選擇很重要。
同時,朝鮮專利第10-1405725號揭示一種有機
發光裝置,其包括經芳基或雜芳基取代之胺衍生物作為發光層之主體,且進一步揭示能夠視情況用作除胺衍生物以外之主體之某些主體。然而,以上公開案未表明藉由與使用唯一主體化合物相比組合具有特定結構之主體來提高發光效率。
就此而言,本發明者已發現與使用習知之唯一主體材料相比,可藉由使用複數種主體材料實現提高之效率,所述複數種主體材料包括經萘基-苯基及芳基取代之胺-咔唑衍生物及二-C-苯并咔唑衍生物作為主體。
本發明之目標為提供一種具有高發光效率及長久壽命之有機電致發光裝置。
本發明者發現以上目標可藉由一種有機電致發光裝置達成,所述有機電致發光裝置包括至少一個安置於陽極與陰極之間的發光層,其中所述發光層包括主體及磷光摻雜劑,其中所述主體包括複數種主體化合物,其中所述複數種主體化合物中之至少第一主體化合物由下式1表示:
其中L1表示經取代或未經取代之(C6-C30)伸芳基;
Ar表示經取代或未經取代之(C6-C60)芳基;R1至R10各自獨立地表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C6-C60)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基,或經取代或未經取代之單(C6-C30)芳胺基或二(C6-C30)芳胺基;或可鍵聯至鄰近取代基以形成經取代或未經取代之單環或多環(C3-C30)、脂環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換;藉由鍵聯至鄰近取代基形成之(雜)芳族環選自由以下組成之群:苯、環戊二烯、吲哚、茚、苯并呋喃及苯并噻吩,且可經(C1-C10)烷基或(C6-C15)芳基取代;雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子;a表示1至4之整數;b表示1至7之整數;其中a及b各自獨立地表示2或大於2之整數,R9及R10中之每一者可相同或不同;且所述複數種主體化合物中之至少第二主體化合物由下式2表示:
其中L2表示單鍵、經取代或未經取代之含氮(5至18員)伸雜芳基,或經取代或未經取代之(C6-C30)伸芳基;Ma表示經取代或未經取代之含氮(5至30員)雜芳基;R11及R12各自獨立地表示氫、氘、鹵素、氰基、羧基、硝基、羥基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C3-C30)環烯基、經取代或未經取代之(3至7員)雜環烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、-NR13R14或-SiR15R16R17;R13至R17各自獨立地表示經取代或未經取代之(C6-C30)芳基或經取代或未經取代之(3至30員)雜芳基;(伸)雜芳基)及雜環烷基含有至少一個選自B、N、O、S、Si及P之雜原子;及c及d表示1至6之整數;其中c及d各自獨立地表示2或大於2之整數,R11及R12中之每一者可相同或不同。
根據本發明,提供具有高效及長久壽命之有機電致發光裝置。另外,本發明之有機電致發光裝置可以用於製造顯示裝置或照明裝置。
在下文中,將詳細描述本發明。然而,以下描述意欲闡明本發明,且不意欲以任何方式限制本發明之範疇。
本發明者已發現與在發光層中使用習知主體材料相比,當使用經萘基-苯基及芳基取代之胺-咔唑衍生物之第一主體,與二-C-苯并咔唑衍生物的第二主體之組合作為主體時,提供經改良之效果。
具體言之,第二主體單獨展示因照度變得較高而致之降低的效率(在下文中,稱為「衰減」特徵)及劣化之壽命特徵。然而,當使第二主體與經萘基-苯基及芳基取代之胺-咔唑衍生物之第一主體組合時,衰減特徵得以改良,且壽命特徵亦大大地改良。
在高照度下維持高效率之理由為滿足需要日益高之解析度之當前顯示器工業。在需要較小像素之當前趨勢下,當即使高照度下維持亦高效率時可實現高解析度。與包括在無聯苯基或苯基的情況下經萘基取代之胺相比,經改良之壽命特徵藉由包括經「萘基-苯基」取代之胺作為第一主體來實現。
在式1中,Ar較佳表示經取代或未經取代之(C6-C20)芳基,更佳地經取代或未經取代之苯基、經取代或未經取代之聯苯基、經取代或未經取代之萘基苯基,或經取代或未經取代之茀基,且甚至更佳地未經取代之苯基、未經取代之聯苯基、未經取代之萘基苯基或經二甲基取代之茀基。
在式1中,L1較佳表示經取代或未經取代之(C6-C20)伸芳基;更佳地經取代或未經取代之伸苯基、經取代或未經取代之伸聯苯基、經取代或未經取代之伸萘基、經取代或未經取代之萘基伸苯基、經取代或未經取代之苯基伸萘基,或經取代或未經取代之伸茀基,且甚至更佳地未經取代
之伸苯基、未經取代之伸聯苯基、未經取代之伸萘基、經二甲基取代之伸茀基、未經取代之萘基伸苯基或未經取代之苯基伸萘基。
在式1中,R1至R10較佳各自獨立地表示氫,或可鍵聯至鄰近取代基以形成經取代或未經取代之單環或多環(C3-C30)芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換;其中經取代或未經取代之單環或多環(C3-C30)芳族環可為未經取代之苯環、經二甲基取代之環戊二烯環、經二甲基取代之茚環、未經取代之苯并噻吩環或未經取代之苯并呋喃環。
在式2中,Ma較佳表示經取代或未經取代之含氮(5至20員)雜芳基;更佳地經取代或未經取代之三嗪基、經取代或未經取代之嘧啶基、經取代或未經取代之吡啶基、經取代或未經取代之喹唑啉基、經取代或未經取代之喹喏啉基、經取代或未經取代之二苯并喹喏啉基,或經取代或未經取代之喹啉基;且甚至更佳地經取代三嗪基、經取代嘧啶基、經取代吡啶基、經取代喹唑啉基、經取代喹喏啉基、未經取代之二苯并喹喏啉基或經取代喹啉基。
在式2中,L2較佳表示單鍵、經取代或未經取代之含氮(5至15員)伸雜芳基,或經取代或未經取代之(C6-C18)伸芳基;更佳地單鍵、經取代或未經取代之伸苯基、經取代或未經取代之伸聯苯基、經取代或未經取代之伸萘基、經取代或未經取代之伸咔唑基,或經取代或未經取代之伸吡啶基;且甚至更佳地單鍵、經取代伸苯基、未經取代之伸聯苯基、未經取代之伸萘基、未經取代之伸咔唑基或未經取代之
伸吡啶基;在式2中,R11及R12較佳各自獨立地表示氫或經取代或未經取代之(C6-C20)芳基;且更佳各自獨立地表示氫、未經取代之苯基或未經取代之萘基。
本文中,「(C1-C30)烷基」意欲為構成鏈之具有1至30個碳原子之直鏈或分支鏈烷基,其中碳原子數目較佳為1至20,更佳為1至10,且包含甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基等;「(C2-C30)烯基」意欲為構成鏈之具有2至30個碳原子之直鏈或分支鏈烯基,其中碳原子數目較佳為2至20,更佳為2至10,且包含乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等;「(C2-C30)炔基」意欲為構成鏈之具有2至30個碳原子之直鏈或分支鏈炔基;其中碳原子數目較佳為2至20,更佳為2至10,且包含乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等;「(C3-C30)環烷基」為具有3至30個環主鏈碳原子之單環或多環烴,其中碳原子數目較佳為3至20,更佳為3至7,且包含環丙基、環丁基、環戊基、環己基等;「(3至7員)雜環烷基」為具有3至7個、較佳5至7個環主鏈原子之環烷基,包含至少一個選自B、N、O、S、Si及P、較佳O、S及N之雜原子,且包含四氫呋喃、吡咯啶、硫、四氫哌喃等;「(C6-C30)(伸)芳基」為衍生自具有6至30個環主鏈碳原子之芳族烴之單環或稠環,其中碳原子數目較佳為6至20,更佳為6至15,且包含苯基、聯苯基、聯三苯、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、
茀蒽基等;「(3至30員)(伸)雜芳基」為具有3至30個環主鏈原子、較佳3至20個環主鏈原子,且更佳3至15個環主鏈原子之芳基,包含至少一個、較佳1至4個選自由B、N、O、S、Si及P組成之群之雜原子;可為單環或經至少一個苯環縮合之稠環;可部分飽和;可為藉由經單鍵將至少一個雜芳基或芳基鍵聯至雜芳基來形成之一者;且包含單環型雜芳基,其包含呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋呫基、吡啶基、吡嗪基、嘧啶基、噠嗪基等,及稠環型雜芳基,其包含苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異噁唑基、苯并噁唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、啉基、喹唑啉基、喹喏啉基、咔唑基、啡噁嗪基、啡啶基、苯并間二氧雜環戊烯基等;「含氮(5至18員)(伸)雜芳基」表示具有5至18個環主鏈原子、較佳5至17個環主鏈原子及、更佳5至15個環主鏈原子之芳基,含有至少一個、較佳1至4個氮作為雜原子,可為單環或經至少一個苯環縮合之稠環;可部分飽和;可為藉由經單鍵將至少一個雜芳基或芳基鍵聯至雜芳基形成之一者;且包含單環型雜芳基,諸如吡咯基、咪唑基、吡唑基、三嗪基、四嗪基、三唑基、四唑基、吡啶基、吡嗪基、嘧啶基、噠嗪基等,及稠環型雜芳基,諸如苯并咪唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、啉基、喹唑啉基、喹喏啉基、咔唑基、啡啶基等。此外,「鹵素」包
含F、Cl、Br及I。
本文中,表述「經取代或未經取代之」中之「經取代」意謂某一官能基中的氫原子經另一個原子或基團(亦即取代基)置換。式1及2中之經取代烷基、經取代烯基、經取代炔基、經取代環烷基、經取代環烯基、經取代雜環烷基、經取代(伸)芳基、經取代(伸)雜芳基、經取代三烷基矽烷基、經取代三芳基矽烷基、經取代二烷基芳基矽烷基、經取代單芳胺基或二芳胺基,及經取代單環或多環、脂環或芳族環之取代基各自獨立地為選自由以下組成之群之至少一個:氘;鹵素;氰基;羧基;硝基;羥基;(C1-C30)烷基;鹵基(C1-C30)烷基;(C2-C30)烯基;(C2-C30)炔基;(C1-C30)烷氧基;(C1-C30)烷硫基;(C3-C30)環烷基;(C3-C30)環烯基;(3至7員)雜環烷基;(C6-C30)芳氧基;(C6-C30)芳基硫基;未經取代或經(C6-C30)芳基取代之(3至30員)雜芳基;未經取代或經(3至30員)雜芳基取代之(C6-C30)芳基;三(C1-C30)烷基矽烷基;三(C6-C30)芳基矽烷基;二(C1-C30)烷基(C6-C30)芳基矽烷基;(C1-C30)烷基二(C6-C30)芳基矽烷基;胺基;單(C1-C30)烷胺基或二(C1-C30)烷胺基;單(C6-C30)芳胺基或二(C6-C30)芳胺基;(C1-C30)烷基(C6-C30)芳胺基;(C1-C30)烷基羰基;(C1-C30)烷氧基羰基;(C6-C30)芳基羰基;二(C6-C30)芳基硼基;二(C1-C30)烷基硼基;(C1-C30)烷基(C6-C30)芳基硼基;(C6-C30)芳基(C1-C30)烷基;及(C1-C30)烷基(C6-C30)芳基。
式1之第一主體化合物可選自由以下化合物組成之群,但不限於此:
式2之第二主體化合物可選自由以下化合物組成之群,但不限於此:
本發明之有機電致發光裝置包括陽極;陰極;及至少一個安置於陽極與陰極之間的發光層,其中所述發光層包括主體及磷光摻雜劑;所述主體包括複數種主體化合物;且所述複數種主體化合物中之至少第一主體化合物由式1表示,其具有經萘基-苯基及芳基取代之胺-咔唑結構,且第二主體化合物由式2表示,其具有包括含氮雜芳基之二-C-苯并咔唑結構。
發光層指示發射光之層,且可為單層或由兩層或
更多層沈積之多層。摻雜化合物之摻雜量以主體化合物及摻雜化合物之總量計較佳小於20wt%。
包括於本發明之有機電致發光裝置中之摻雜劑較佳為至少一種磷光摻雜劑。用於本發明之有機電致發光裝置之磷光摻雜劑材料不受限制,但可較佳選自銥(Ir)、鋨(Os)、銅(Cu)以及鉑(Pt)之金屬化錯合物化合物,更佳選自銥(Ir)、鋨(Os)、銅(Cu)以及鉑(Pt)之鄰位金屬化錯合物化合物,且甚至更佳為鄰位金屬化的銥錯合物化合物。
較佳地,磷光摻雜劑可選自由經以下式101至103表示之化合物組成之群。
其中L選自以下結構:
R100表示氫或經取代或未經取代之(C1-C30)烷基;R101至R109及R111至R123各自獨立地表示氫、氘、鹵素、未經取代或經氘或鹵素取代之(C1-C30)烷基、氰基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基,或經取代或未經取代之(C6-C30)芳基;R106至R109可鍵聯至鄰近
取代基以形成經取代或未經取代之單環或多環(C3-C30)、脂環或(雜)芳族環,例如二苯并呋喃;R120至R123可鍵聯至鄰近取代基以形成經取代或未經取代之單環或多環(C3-C30)、脂環或芳族環,例如喹啉;R124至R127各自獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基,或經取代或未經取代之(C6-C30)芳基;且在R124至R127為芳基時,R124至R127之鄰近取代基可彼此鍵聯以形成經取代或未經取代之單環或多環(C3-C30)、脂環或(雜)芳族環,例如茀、二苯并噻吩或二苯并呋喃;R201至R211各自獨立地表示氫、氘、鹵素、未經取代或經氘或鹵素取代之(C1-C30)烷基,或未經取代或經氘或烷基取代之(C6-C30)芳基;且R208至R211可鍵聯至鄰近取代基以形成經取代或未經取代之單環或多環(C3-C30)、脂環或芳族環或雜芳環,例如茀、二苯并噻吩或二苯并呋喃;r及s各自獨立地表示1至3之整數;在r或s為2或大於2之整數時,R100中之每一者可相同或不同;且e表示1至3之整數。
具體而言,磷光摻雜劑材料包含以下各者:
本發明之有機電致發光裝置可在有機層處進一
步包括至少一種選自由以下組成之群之化合物:基於芳基胺之化合物及基於苯乙烯基芳基胺之化合物。
此外,在本發明之有機電致發光裝置中,有機層可進一步包括至少一種選自由以下組成之群的金屬:週期表之第1族金屬、第2族金屬、第4週期過渡金屬、第5週期過渡金屬、鑭系元素及d-過渡元素的有機金屬,或包括所述金屬之至少一種錯合物化合物。
較佳地,在本發明之有機電致發光裝置中,至少一個層(在下文中,「表面層」)可置於一個或兩個電極之內表面上,所述層選自硫族化合物層、金屬鹵化物層及金屬氧化物層。具體而言,具有矽或鋁之硫族化物(包含氧化物)層較佳置於電致發光中間層之陽極表面上,且金屬鹵化物層或金屬氧化物層較佳置於電致發光中間層之陰極表面上。此類表面層為有機電致發光裝置提供操作穩定性。較佳地,硫族化合物包含SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等;金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等;且金屬氧化物包含Cs2O、Li2O、MgO、SrO、BaO、CaO等。
電洞注入層、電洞傳輸層、電子阻擋層或其組合可安置於陽極與發光層之間。電洞注入層可由兩層或更多層構成,以便降低自陽極向電洞傳輸層或電子阻擋層注入電洞之能量障壁(或注入電洞之電壓)。所述層中之每一者可包括兩種或更多種化合物。電洞傳輸層或電子阻擋層可由兩層或更多層構成。
電子緩衝層、電洞阻擋層、電子傳輸層、電子注入層或其組合可安置於發光層與陰極之間。電子緩衝層可由
兩層或更多層構成,以便控制電子注入且改良發光層與電子注入層之間之界面的特徵。所述層中之每一者可包括兩種或更多種化合物。電洞阻擋層或電子傳輸層可由兩層或更多層構成,且所述層中之每一者可包括兩種或更多種化合物。
在本發明之有機電致發光裝置中,電子傳輸化合物及還原性摻雜劑之混合區、或電洞傳輸化合物及氧化性摻雜劑之混合區可以置於一對電極之至少一個表面上。在此情況下,電子傳輸化合物還原成陰離子,且因此變得更容易自混合區域注入及傳輸電子至電致發光介質。此外,電洞傳輸化合物氧化成陽離子,且因此變得更容易自混合區域注入及傳輸電洞至電致發光介質。較佳地,氧化性摻雜劑包含各種路易斯酸(Lewis acid)及受體化合物;且還原性摻雜劑包含鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合物。還原性摻雜劑層可用作電荷產生層以製備具有兩個或更多個發光層且發射白光之電致發光裝置。
為了形成本發明之有機電致發光裝置的每一層,可使用乾式成膜方法,例如真空蒸發、濺射、電漿、離子電鍍方法等,或濕式成膜方法,例如旋轉塗佈、浸漬塗佈、流動塗佈方法等。本發明之第一主體化合物及第二主體化合物可為藉由共蒸發或混合蒸發形成之膜。
當使用濕式成膜方法時,薄膜可藉由將形成每一層之材料溶解或擴散至任何適合溶劑中來形成,所述溶劑諸如乙醇、氯仿、四氫呋喃、二噁烷等。溶劑可為形成每一層之材料可溶解或擴散於其中且不存在成膜能力問題的任何溶劑。
另外,本發明之有機電致發光裝置可用於製造顯示裝置或照明裝置。
在下文中,將參照以下實例詳細闡述包括本發明之主體化合物之裝置的發光特性。
[裝置實例1-1]藉由共蒸發作為主體之本發明之第一主體化合物及第二主體化合物來產生OLED裝置
按以下產生包括本發明之所述複數種主體化合物之OLED裝置。使有機電致發光裝置(OLED)(Geomatec)之玻璃基板上的透明電極氧化銦錫(ITO)薄膜(10Ω/sq)經歷依序使用丙酮、乙醇及蒸餾水之超音波洗滌,且接著儲存在異丙醇中。接著,將ITO基板安裝於真空氣相沈積設備之基板固持器上。將化合物HIL引入真空氣相沈積設備之單元中,且隨後將設備之腔室中之壓力控制為10-6托,且藉由將電流施加至所述單元來蒸發,藉此在ITO基板上形成厚度為90nm之第一電洞注入層。其後,將化合物HITL接著引入真空氣相沈積設備之另一單元中,且藉由將電流施加至所述單元來蒸發,藉此在第一電洞注入層上形成厚度為5nm之第二電洞注入層。將化合物HTL1引入真空氣相沈積設備之一個單元中,且藉由將電流施加至所述單元來蒸發,藉此在第二電洞注入層上形成厚度為10nm之第一電洞傳輸層。隨後將下表1中展示之化合物HTL(化合物HTL5)引入真空氣相沈積設備之另一單元中,且藉由將電流施加至所述單元來蒸發,藉此在第一電洞傳輸層上形成厚度為60nm之第二電洞傳輸層。在形成電洞注入層及電洞傳輸層之後,接著如下沈積發光層。作為主體材料,將下表1中展示之第一主體化合物及
第二主體化合物分別引入真空氣相沈積設備之兩個單元中。將化合物D-71作為摻雜劑引入另一單元中。兩種主體化合物以1:1之相同速率蒸發,同時摻雜劑自主體化合物以不同速率蒸發,使得摻雜劑以按主體及摻雜劑之總量計2wt%之摻雜量沈積,以在第二電洞傳輸層上形成厚度為40nm之發光層。接著,將化合物ETL及化合物EIL在真空氣相沈積設備之其他兩個單元上以1:1之速率蒸發,以在發光層上形成厚度為35nm之電子傳輸層。在電子傳輸層上沈積厚度為2nm之化合物EIL作為電子注入層之後,隨後藉由另一真空氣相沈積設備在電子注入層上沈積厚度為80nm之鋁陰極。由此,產生OLED裝置。
在1,000尼特照度下量測下表1中之驅動電壓。衰減表示1,000尼特下與5,000尼特下之間的效率之差異,亦即「衰減=△效率(1,000尼特-5,000尼特)=1,000尼特照度下之效率-5,000尼特照度下之效率」,其指示隨著照度增加,有多少效率降低。較小之衰減值為較佳的。壽命為在維持恆定溫度及濕度之系統中在5,000尼特及恆定電流下,照度自100%降低至97%所消耗之時間。
[產生裝置實例1-2、1-3、2-1、3-1至3-6、4-1、5-1、7-1及7-2,及比較實例1-1、2-1、3-1、4-1、5-1及7-1之OLED裝置]
以與裝置實例1-1中之相同之方式產生OLED裝置,但僅表1中所展示之化合物用作第一主體、第二主體及化合物HTL。
[產生裝置實例8-1、9-1、10-1、10-2、12-1、13-1及14-1,及比較實例8-1、9-1、10-1、12-1、13-1及14-1之OLED裝置]
以與裝置實例1-1中之相同之方式產生OLED裝置,但僅表1中所展示之化合物用作第一主體、第二主體及化合物HTL,形成厚度為80nm之第一電洞注入層(HIL),形成厚度為30nm之電子傳輸層(ETL),且將摻雜量改變至3wt%。
[產生裝置實例15-1至15-6及比較實例15-1之OLED裝置]
以與裝置實例1-1中之相同之方式產生OLED裝置,但僅表2中所展示之化合物用作第一主體、第二主體及化合物HTL,且化合物D-134用作摻雜劑。壽命為在5,000尼特及恆定電流下照度自100%降低至99%所消耗之時間。
本發明之有機電致發光裝置包括發光層,所述發光層包括複數種主體化合物及磷光摻雜劑,其中所述複數種主體化合物中之至少第一主體化合物具有萘基-苯基及芳基經取代之胺-咔唑結構,且第二主體化合物具有包括特定含氮雜芳基之二-C-苯并咔唑結構。可看到,與習知裝置相比,藉由具有以上結構,高效率在高照度下維持,且壽命經高度提高。
Claims (7)
- 一種有機電致發光裝置,其包括至少一個安置於陽極與陰極之間的發光層,其中所述發光層包括主體及磷光摻雜劑,其中所述主體包括複數種主體化合物,其中所述複數種主體化合物中之至少第一主體化合物由下式1表示:
- 如申請專利範圍第1項所述的有機電致發光裝置,其中式1中之Ar表示經取代或未經取代之(C6-C20)芳基。
- 如申請專利範圍第1項所述的有機電致發光裝置,其中式2中之Ma表示經取代或未經取代之含氮(5至20員)雜芳基。
- 如申請專利範圍第1項所述的有機電致發光裝置,其中式2中之Ma表示經取代或未經取代之三嗪基、經取代或未經取代之嘧啶基、經取代或未經取代之吡啶基、經取代或未經取代之喹唑啉基、經取代或未經取代之喹喏啉基、經取代或未經取代之二苯并喹喏啉基,或經取代或未經取代之喹啉基。
- 如申請專利範圍第1項所述的有機電致發光裝置,其中式1及2中之所述經取代烷基、所述經取代烯基、所述經取代炔基、所述經取代環烷基、所述經取代環烯基、所述經取代雜環烷基、所述經取代(伸)芳基、所述經取代(伸)雜芳基、所述經取代三烷基矽烷基、所述經取代三芳基矽烷基、所述經取代二烷基芳基矽烷基、所述經取代單芳胺基或二芳胺基,及所述經取代單環或多環、脂環或芳族環之取代基各自獨立地為選自由以下組成之群之至少一個:氘;鹵素;氰基;羧基;硝基;羥基;(C1-C30)烷基;鹵基(C1-C30)烷基;(C2-C30)烯基;(C2-C30)炔基;(C1-C30) 烷氧基;(C1-C30)烷硫基;(C3-C30)環烷基;(C3-C30)環烯基;(3至7員)雜環烷基;(C6-C30)芳氧基;(C6-C30)芳基硫基;未經取代或經(C6-C30)芳基取代之(3至30員)雜芳基;未經取代或經(3至30員)雜芳基取代之(C6-C30)芳基;三(C1-C30)烷基矽烷基;三(C6-C30)芳基矽烷基;二(C1-C30)烷基(C6-C30)芳基矽烷基;(C1-C30)烷基二(C6-C30)芳基矽烷基;胺基;單(C1-C30)烷胺基或二(C1-C30)烷胺基;單(C6-C30)芳胺基或二(C6-C30)芳胺基;(C1-C30)烷基(C6-C30)芳胺基;(C1-C30)烷基羰基;(C1-C30)烷氧基羰基;(C6-C30)芳基羰基;二(C6-C30)芳基硼基;二(C1-C30)烷基硼基;(C1-C30)烷基(C6-C30)芳基硼基;(C6-C30)芳基(C1-C30)烷基;及(C1-C30)烷基(C6-C30)芳基。
- 如申請專利範圍第1項所述的有機電致發光裝置,其中所述由式1表示之化合物係選自由以下組成之群:
- 如申請專利範圍第1項所述的有機電致發光裝置,其中所述由式2表示之化合物係選自由以下組成之群:
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JP2018521506A (ja) | 2018-08-02 |
TWI688556B (zh) | 2020-03-21 |
JP6945457B2 (ja) | 2021-10-06 |
CN107635964B (zh) | 2021-11-09 |
EP3322693A4 (en) | 2019-01-16 |
KR102576858B1 (ko) | 2023-09-12 |
US20180182973A1 (en) | 2018-06-28 |
EP3322693A1 (en) | 2018-05-23 |
US10490752B2 (en) | 2019-11-26 |
CN107635964A (zh) | 2018-01-26 |
EP3322693B1 (en) | 2020-02-12 |
WO2016204394A1 (en) | 2016-12-22 |
KR20160149994A (ko) | 2016-12-28 |
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