TWI699365B - 多組分主體材料及包括所述主體材料之有機電致發光裝置 - Google Patents
多組分主體材料及包括所述主體材料之有機電致發光裝置 Download PDFInfo
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- TWI699365B TWI699365B TW105118037A TW105118037A TWI699365B TW I699365 B TWI699365 B TW I699365B TW 105118037 A TW105118037 A TW 105118037A TW 105118037 A TW105118037 A TW 105118037A TW I699365 B TWI699365 B TW I699365B
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- unsubstituted
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- alkyl
- aryl
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- 239000000463 material Substances 0.000 title description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 239000002019 doping agent Substances 0.000 claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 36
- 125000005104 aryl silyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 238000005401 electroluminescence Methods 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000001769 aryl amino group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- -1 fused tetraphenyl Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Chemical group 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 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 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 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
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy 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
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- 125000005577 anthracene group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 6
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 abstract description 5
- QJTQKPNNQVLHHO-UHFFFAOYSA-N 9h-carbazole;1h-indole Chemical compound C1=CC=C2NC=CC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 QJTQKPNNQVLHHO-UHFFFAOYSA-N 0.000 abstract description 5
- QZFAEVGFWRXLOU-UHFFFAOYSA-N 1-benzofuran;9h-carbazole Chemical compound C1=CC=C2OC=CC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 QZFAEVGFWRXLOU-UHFFFAOYSA-N 0.000 abstract description 4
- MOVXBYGUSGMDNK-UHFFFAOYSA-N 1-benzothiophene 9H-carbazole Chemical group C1=CC=C2SC=CC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 MOVXBYGUSGMDNK-UHFFFAOYSA-N 0.000 abstract description 4
- UGPNGFWKKRUHPH-UHFFFAOYSA-N 9h-carbazole;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 UGPNGFWKKRUHPH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 93
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000007740 vapor deposition Methods 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 6
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 0 CC1(C(*)=C(*)C(c2c(*3*)c(*)c(*)c(*I)c2*)=C3C(*)=C1*)ICc1c(*)c(-c2c(*3*)c(*)c(*)c(*)c2[*-])c3c(*)c1* Chemical compound CC1(C(*)=C(*)C(c2c(*3*)c(*)c(*)c(*I)c2*)=C3C(*)=C1*)ICc1c(*)c(-c2c(*3*)c(*)c(*)c(*)c2[*-])c3c(*)c1* 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer 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
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 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
- 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
- 150000002739 metals Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 125000006651 (C3-C20) cycloalkyl group Chemical group 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 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
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- 125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 description 1
- 125000006835 (C6-C20) arylene group Chemical group 0.000 description 1
- 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
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 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
- 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
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 125000005874 benzothiadiazolyl group Chemical group 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
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 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
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 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
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- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 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 compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Abstract
本發明係關於一種有機電致發光裝置,其包括至少一個介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;所述主體包括多種主體化合物;所述多種主體化合物中之至少一種第一主體化合物具有含氮雜環連接基團結構,所述連接基團鍵結於吲哚-咔唑、茚-咔唑、苯并呋喃-咔唑或苯并噻吩-咔唑殘基之咔唑的氮原子;以及具有咔唑-芳基-咔唑或咔唑-咔唑結構的第二主體化合物。根據本發明,藉由使用與習知有機電致發光裝置不同的特定多組分主體,提供壽命顯著提高之有機電致發光裝置。
Description
本發明係關於一種多組分主體材料及包括所述材料之有機電致發光裝置。
電致發光裝置(EL裝置)為自發光裝置,其優點在於提供較寬視角、較高對比度及較快反應時間。第一有機EL裝置由Eastman Kodak藉由使用小芳族二胺分子及鋁錯合物作為用於形成發光層之材料而開發[《應用物理學快報(Appl.Phys.Lett.)》51,913,1987]。
有機電致發光裝置為藉由向有機電致發光材料施加電將電能變成光的裝置,且一般具有包括陽極、陰極及介於陽極與陰極之間的有機層的結構。有機EL裝置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(其包括主體及摻雜劑材料)、電子緩衝層、電洞阻擋層、電子傳輸層、電子注入層等,且用於有機層之材料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。在有機EL裝置中,由於施加了電壓,電洞自陽極注入發光層,電子自陰極注入發光層,且藉由電洞與電子的再結合形成高能量之激子。藉由此能量,有機發光化合物達到激發態,且由於有機發光化合物之激發態回到基態產生之能量發射光而發光。
決定有機EL裝置的發光效率的最重要因素為發光材料。發光材料必須具有高量子效率、高電子及電洞遷移率,且形成之發光材料層必須均勻及穩定。發光材料視發光顏色而分類為發藍光材料、發綠光材料及發紅光材料,另外以及發黃光材料或發橙光材料。另外,發光材料亦可根據其功能分為主體及摻雜劑材料。最近,開發具有高效率及長壽命的有機EL裝置成為迫切的問題。具體而言,考慮中等或大尺寸OLED面板的EL特徵需求,必須迫切地開發特徵比習知材料好的材料。充當固態溶劑且轉移能量之主體材料需要具有高純度及適於真空沈積之分子量。此外,主體材料需要具有實現熱穩定性之高玻璃轉移溫度及高熱分解溫度、實現長壽命之高電化學穩定性、容易形成非晶形薄膜、與相鄰層之材料良好黏著及不遷移至其他層。
發光材料可以主體與摻雜劑之組合的形式使用來提高色純度、發光效率及穩定性。一般而言,具有極佳特徵之EL裝置具有包括藉由將摻雜劑摻雜至主體形成的發光層。因為當使用摻雜劑/主體材料系統作為發光材料時,主體材料極大地影響EL裝置的效率及壽命,因此其選擇是至關重要的。
韓國專利申請公開案第10-2015-0003658號揭示
使用多組分主體之有機光電元件及顯示裝置,其中具有以下結構之化合物用作第一主體化合物:其中雜芳基鍵結於吲哚-咔唑殘基之各氮原子,其中6員雜芳基環直接連接至氮原子使6員環之取代基連接至間位中之每一個;以及咔唑-咔唑衍生物用作主體組合之第二主體化合物。另外,韓國專利第10-1502316號為本發明的申請者之專利,其係關於多組分主體及包括所述主體之有機電致發光裝置,其使用作為第一主體化合物的咔唑-芳基-咔唑衍生物以及具有含氮雜芳基鍵結於咔唑之氮原子(經芳基)的結構的化合物。
本發明者發現藉由使用具有含氮雜環連接基團鍵結於吲哚-咔唑、茚-咔唑、苯并呋喃-咔唑或苯并噻吩-咔唑殘基之咔唑之氮原子的結構的第一主體化合物及咔唑-芳基-咔唑或咔唑-咔唑衍生物之第二主體化合物,包括所述主體組合之有機電致發光裝置可提供相較於使用習知主體材料之裝置延長壽命的作用。
本發明之目標為提供具有極佳效率及長壽命之有機電致發光裝置。
本發明者發現上述目標可以藉由包括至少一個介於陽極與陰極之間的發光層的有機電致發光裝置實現,其中發光層包括主體及磷光摻雜劑;主體包括多種主體化合物;多種主體化合物之至少一第一主體化合物由下式1表示;以及由下式2表示之第二主體化合物:
其中Z表示NR4、CR5R6、O或S;X1’至X4’各自獨立地表示N或C(R7),X1’至X4’中之一者或多者為N;Y1至Y3各自獨立地表示N或C(R8),Y1至Y3中之兩者或更多者為N;R1至R8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(C6-C30)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(C3-C30)環烷基、經取代或未經取代之(C1-C30)烷氧基、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二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、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單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基;或可與相鄰取代基連接形成經取代或未經取代之單環或多環(C3-C30)脂環族環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換;a及b各自獨立地表示整數1至4;c表示1或2;其中a、b或c為整數2或更大,各R1、各R2或各R3可相同或不同;以及所述雜芳基含有至少一個選自B、N、O、S、Si以及P之雜原子。
其中A1及A2各自獨立地表示經取代或未經取代之(C6-C30)芳基;L1表示單鍵或經取代或未經取代之(C6-C30)伸芳基;以及X1至X16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或二(C6-C30)芳基胺基;或相鄰取代基可以彼此連接形成經取代或未經取代之單環或多環(C3-C30)脂環族環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換。
根據本發明,提供具有高效率及長壽命之有機電致發光裝置,且可製造使用所述有機電致發光裝置之顯示裝置或照明裝置。
在下文中,將詳細地描述本發明。然而,以下描述打算解釋本發明,並且不打算以任何方式限制本發明之範疇。
其中R1至R3、X1’至X4’、Z以及a至c如式1中所定義。
其中R1至R3、Z以及a至c如式1中所定義。
其中R1、R2、Z、a以及b如式1中所定義。
其中A1、A2、L1以及X1至X16如式2中所定義。
在上式1中,R1至R8較佳各自獨立地表示氫、氘、經取代或未經取代之(C1-C20)烷基、經取代或未經取代之(C6-C20)芳基、經取代或未經取代之3至20員雜芳基、經取代或未經取代之(C3-C20)環烷基、經取代或未經取代之(C1-C20)烷氧基、經取代或未經取代之三(C1-C20)烷基矽烷基、經取代或未經取代之二(C1-C20)烷基(C6-C20)芳基矽烷基、經取代或未經取代之(C1-C20)烷基二(C6-C20)芳基矽烷基、經取代或未經取代之三(C6-C20)芳基矽烷基、經取代或未經取代之單或二(C1-C20)烷基胺基、經取代或未經取代之單或二(C6-C20)芳基胺基或經取代或未經取代之(C1-C20)烷基(C6-C20)芳基胺基;或可與相鄰取代基連接形成經取代或未經取代之單環或多環(C3-C20)脂環族環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換;以及更佳各自獨立地表示氫、氘、經取代或未經取代之(C1-C10)烷基、經取代或未經取代之(C6-C15)芳基、經取代或未經取代之3到15員雜芳基、經取代或未經取代之(C3-C15)環烷基、經取代或未經取代之(C1-C10)烷氧基、經取代或未經取代之三(C1-C10)烷基矽烷基、經取代或未經取代之二(C1-C10)烷基(C6-C15)芳基矽烷基、經取代或未經取代之(C1-C10)烷基二(C6-C15)芳基矽烷基、經取代或未經取代之三(C6-C15)芳基矽烷基、經取代或未經取代之單或二(C1-C10)烷基胺基、經取代或未經取代之單或二(C6-C15)芳基胺基或經取代或未經取代之(C1-C10)烷基(C6-C15)芳基胺基;或可與相鄰取代基連接形成經取代或未經取代之單環或多環(C3-C15)脂環族環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換。
在上述式2中,A1及A2較佳各自獨立地表示e經取代或未經取代之(C6-C20)芳基,且更佳各自獨立地表示經取代或未經取代之苯基、聯苯基、三聯苯基、萘基、茀基、苯并茀基、菲基、蒽基、茚基、三亞苯基、芘基、稠四苯基、苝基、基以及茀蒽基。
其中
Xi至Xp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或二(C6-C30)芳基胺基;或相鄰取代基可以彼此連接形成經取代或未經取代之單環或多環(C3-C30)脂環族環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換。
較佳地,在式18至式30中,Xi至Xp較佳各自獨立地表示氫、氘、經取代或未經取代之(C1-C20)烷基、經取代或未經取代之(C2-C20)烯基、經取代或未經取代之(C2-C20)炔基、經取代或未經取代之(C3-C20)環烷基、經取代或未經取代之(C6-C20)芳基、經取代或未經取代之3至20員雜芳基、經取代或未經取代之三(C1-C20)烷基矽烷基、經取代或未經取代之三(C6-C20)芳基矽烷基、經取代或未經取代之二(C1-C20)烷基(C6-C20)芳基矽烷基或經取代或未經取代之單或二(C6-C20)芳基胺基;或相鄰取代基可以彼此連接形成經取代或未經取代之單環或多環(C3-C20)脂環族環或芳族環,其碳原子可經至少一個選自氮、氧及硫之雜原子置換。
此處,「(C1-C30)烷基」意謂具有1至30個構成鏈之碳原子的直鏈或分支鏈烷基,其中碳原子數較佳為1至20,更佳1至10,並且包含甲基、乙基、正丙基、異丙基、
正丁基、異丁基、第三丁基等;「(C2-C30)烯基」意謂具有2至30個構成鏈之碳原子的直鏈或分支鏈烯基,其中碳原子數較佳為2至20,更佳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」意謂具有2至30個構成鏈之碳原子地直鏈或分支鏈炔基,其中碳原子數較佳為2至20,更佳2至10,並且包含乙炔基、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;「(C1-C30)烷氧基」意謂具有1至30個構成鏈之碳原子的直鏈或分支鏈烷基,其中碳原子數較佳為1至20,更佳1至10,並且包含甲氧基、乙氧基、丙氧基、異丙氧基、1-乙基丙氧基等;「(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,其中碳原子數較佳為3至20,更佳3至7,並且包含環丙基、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以及P,較佳O、S以及N之雜原子,並且包含四氫呋喃、吡咯啶、硫雜環戊烷、四氫哌喃等;「(C6-C30)(伸)芳基」為衍生自芳族烴且具有6至30個環主鏈碳原子的單環或稠合環,其中碳原子數較佳為6至20,更佳6至15,並且包含苯基、聯苯基、三聯苯基、萘基、茀基、菲基、蒽基、茚基、三亞苯基、芘基、稠四苯基、苝基、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個環主鏈原子並且更佳3至15個環主鏈原子的芳基,其包含至少一個,較佳1至4個選自由B、N、O、S、Si以及P組成之群的雜原子;為單環或與至少一個苯
環稠合之稠合環;可以部分飽和;可以藉由經單鍵將至少一個雜芳基或芳基連接至雜芳基形成;並且包含單環型雜芳基,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、呋吖基、吡啶基、吡嗪基、嘧啶基、噠嗪基等,以及稠合環型雜芳基,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、喹喔啉基、咔唑基、啡噁嗪基、啡啶基、苯并間二氧雜環戊烯基等。此外,「鹵素」包含F、Cl、Br以及I。
此處,表述「經取代或未經取代」中之「經取代」意謂特定官能基中之氫原子經另一原子或基團(即取代基)置換。在式1及式2中,R1至R8、A1、A2、L1以及X1至X16中之經取代之烷基、經取代之烯基、經取代之炔基、經取代之烷氧基、經取代之環烷基、經取代之三烷基矽烷基、經取代之二烷基芳基矽烷基、經取代之烷基二芳基矽烷基、經取代之三芳基矽烷基、經取代之單或二烷基胺基、經取代之單或二芳基胺基、經取代之烷基芳基胺基、經取代之(伸)芳基、經取代之雜芳基及經取代之單環或多環(C3-C30)脂環族環或芳族環的取代基各自獨立地為選自由以下組成之群的至少一者: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、單或二(C1-C30)烷基胺基、單或二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基基、二(C1-C30)烷基基、(C1-C30)烷基(C6-C30)芳基基、(C6-C30)芳基(C1-C30)烷基以及C1-C30)烷基(C6-C30)芳基。
根據本發明的有機電致發光裝置包括陽極、陰極及至少一個介於陽極與陰極之間的發光層。發光層包括主體及磷光摻雜劑。主體材料包括多種主體化合物,多種主體化合物之至少一第一主體化合物由式1表示,其具有含氮雜環
連接基團鍵結於吲哚-咔唑、茚-咔唑、苯并呋喃-咔唑或苯并噻吩-咔唑殘基之咔唑的氮原子的結構,並且第二主體化合物由式2表示,其具有咔唑-芳基-咔唑或咔唑-咔唑結構。
發光層為發射光之層,並且可以為單層或堆疊有兩個或更多個層的多層。在發光層中,較佳地,基於主體化合物之摻雜化合物的摻雜濃度小於20重量%。
根據本發明之有機電致發光裝置中包括的磷光摻雜劑不受限制,但較佳可選自銥、鋨、銅以及鉑的金屬化錯合物化合物,更佳選自銥、鋨、銅及鉑的鄰位金屬化錯合物化合物,且甚至更佳為鄰位金屬化銥錯合物化合物。
磷光摻雜劑較佳選自由以下式101至式103表示之化合物。
R100表示氫或經取代或未經取代之(C1-C30)烷基;R101至R109以及R111至R123各自獨立地表示氫、氘、鹵素、未經取代或經鹵素取代之(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;R120至R123可與相鄰取代基連接形成經取代或未經取代之單環或多環(C3-C30)脂環族環或芳族環,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;並且其中R124至R127為芳基,R124至R127可以與相鄰取代基連接形成經取代或未經取代之單環或多環(C3-C30)脂環族或(雜)芳族環,例如芴、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、或未經取代或經鹵素取代之(C1-C30)烷基;R208至R211可與相鄰取代基連接形成經取代或未經取代之單環或多環(C3-C30)脂環族、芳族或雜芳族環,例如芴、二苯并噻吩或二苯并呋喃;r及s各自獨立地表示整數1至3;在r或s為2或更大之整數的情況下,各R100可相同或不同;以及e表示整數1至3。
根據本發明之有機電致發光裝置可在有機層中進一步包括至少一種選自由以下組成之群的化合物:基於芳基胺之化合物及基於苯乙烯基芳基胺之化合物。
另外,在根據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:週期表的第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,或包括所述金屬的至少一種錯合物化合物。
根據本發明,至少一個層(在下文中,「表層」)較佳置於一個或兩個電極的內表面上:選自硫族化物層、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的陽極表面上,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的陰極表面上。此類表面層為有機電致發光裝置提供操作穩定性。較佳地,所述硫族化物包含SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等;所述金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等;且所述金屬氧化物包含Cs2O、Li2O、MgO、SrO、BaO、CaO等。
陽極與發光層之間可使用電洞注入層、電洞傳輸層、電子阻擋層或其組合。電洞注入層可使用多層來降低從陽極至電洞傳輸層或電子阻擋層的電洞注入障壁(或電洞注入電壓)。兩種化合物可同時用於各層中。電洞傳輸層及電子
阻擋層亦可由多層形成。
發光層與陰極之間可使用選自電子緩衝層、電洞阻擋層、電子傳輸層或電子注入層的層或由其組合形成之層。電子緩衝層可使用多層來控制電子的注入並且提高發光層與電子注入層之間的界面特徵。兩種化合物可同時用於各層中。電洞阻擋層及電子傳輸層亦可由多層形成,並且各層可包括兩種或更多種化合物。
在根據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域、或電洞傳輸化合物及氧化性摻雜劑的混合區域較佳置於一對電極的至少一個表面上。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。另外,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、稀土金屬以及其混合物。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電致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,諸如真空蒸發、濺射、電漿及離子電鍍方法;或濕式成膜方法,諸如旋塗、浸塗及流塗方法。本發明之第一及第二主體化合物可以共蒸發或混合物蒸發。
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
之材料可以溶解或擴散且不存在成膜能力問題的任何溶劑。
藉由使用本發明之有機電致發光裝置,可產生顯示系統或照明系統。
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:製備OLED裝置,其中將本發明之第一主體化合物及第二主體化合物共蒸發
使用根據本發明之有機電致發光化合物製造OLED裝置。依序使用丙酮、乙醇及蒸餾水對有機發光二極體(OLED)裝置(Geomatec)之玻璃基板上的透明電極氧化銦錫(ITO)薄膜(10Ω/sq)進行超音波洗滌,且接著儲存於異丙醇中。接著,將ITO基板安置於真空氣相沈積設備之基板固持器上。將化合物HI-1引入所述真空氣相沈積設備的單元中,並且接著將所述設備的腔室中之壓力控制在10-6托。此後,向所述單元施加電流以使上述引入之材料蒸發,由此在ITO基板上形成厚度為5nm之電洞注入層。接著,將化合物HT-1引入所述真空氣相沈積設備的另一單元中,且藉由向所述單元施加電流而蒸發,藉此在電洞注入層上形成厚度為95nm的第一電洞傳輸層。接著將化合物HT-2引入所述真空氣相沈積設備的另一單元中,且藉由向所述單元施加電流而蒸發,藉此在第一電洞傳輸層上形成厚度為20nm的第二電洞傳輸層。將表1中之裝置實例1-1之第一及第二主體化合物引入所述真空氣相沈積設備的兩個單元中作為主體,並且將化合物D-74引入另一單元中作為摻雜劑。兩種主體材料以1:1之相同速率蒸發,而摻雜材料以與主體材料不同之速率蒸
發,使得摻雜劑按主體及摻雜劑之總量計以12重量%的摻雜量沈積,以蒸發及在第二電洞傳輸層上形成厚度為30nm之發光層。接著將化合物ET-1引入真空氣相沈積設備的另一單元中並且在發光層上蒸發形成厚度為35nm之電子傳輸層。化合物EI-1在電子傳輸層上沈積為厚度2nm的電子注入層之後,藉由另一真空氣相沈積設備沈積厚度為80nm的Al陰極。從而,製得OLED裝置。
裝置實例1-2至1-9:製備OLED裝置,其中將本發明之第一主體化合物及第二主體化合物共蒸發
以與裝置實例1-1相同之方式製造OLED裝置,但使用表1中裝置實例1-2至1-9的發光層的主體及摻雜劑。
比較例1-1至1-6:製備僅包括本發明之第二主體化合物作為主體的OLED裝置
以與裝置實例1-1相同之方式製造OLED裝置,但使用表1中比較例1-1至1-6之發光層的主體。
比較例1-7:製備僅包括本發明之第一主體化合物作為主體的OLED裝置
以與裝置實例1-1相同之方式製造OLED裝置,但使用表1中比較例1-7之發光層的主體。
比較例2-1:製備包括本發明之第二主體化合物及並非根據本發明之主體化合物作為主體的OLED裝置
以與裝置實例1-1相同之方式製造OLED裝置,但使用表1中比較例2-1之發光層的主體。
裝置實例1-1至1-9、比較例1-1至1-7以及比較例2-1中製造的OLED的在10mA/cm2下的驅動電壓以及在10,000nit下亮度自100%降低至97%所耗費之時間以及恆定電流顯示於下表1中。
裝置實例2:製備OLED裝置,其中將磷光主體材料及本發明之第二主體化合物共蒸發
使用根據本發明之有機電致發光化合物製造OLED裝置。依序使用丙酮、乙醇及蒸餾水對有機發光二極體(OLED)裝置(Geomatec)之玻璃基板上的透明電極氧化銦錫(ITO)薄膜(10Ω/sq)進行超音波洗滌,且接著儲存於異丙醇中。接著,將ITO基板安置於真空氣相沈積設備之基板固持器上。將化合物HI-2引入所述真空氣相沈積設備的單元中,並且接著將所述設備的腔室中之壓力控制到10-6托。此後,向所述單元施加電流以使上述引入之材料蒸發,藉此在ITO基板上形成厚度為80nm之第一電洞注入層。接著將化合物HI-1引入所述真空氣相沈積設備的另一單元中,且藉由向所述單元施加電流蒸發,藉此在第一電洞注入層上形成厚度為5nm的第二電洞注入層。接著,將化合物HT-3引入所述真空氣相沈積設備的另一單元中,且藉由向所述單元施加電流蒸發,藉此在第二電洞注入層上形成厚度為10nm的第一電洞傳輸層。接著將化合物HT-2引入所述真空氣相沈積設備的另一單元中,且藉由向所述單元施加電流蒸發,藉此在第一電洞傳輸層上形成厚度為30nm的第二電洞傳輸層。將化合物H1-71及H2-141引入所述真空氣相沈積設備的兩個單元中作為主體,且將化合物D-102引入另一單元中作為摻雜劑。兩種主體材料以1:1之相同速率蒸發,而摻雜材料以與主體材料不同之速率蒸發,使得摻雜劑按主體及摻雜劑之總量計以10重量%的摻雜量沈積,以蒸發及在第二電洞傳輸層上形成厚度為40nm之發光層。接著分別將化合物ET-2及化合物EI-1引入真空氣相沈積設備的兩個單元中,且在4:6之速率下蒸發在發光層上形成厚度為35nm的電子傳輸層。在電子傳輸層上將化合物EI-1沈積為厚度為2nm的電子注入層之後,藉由另一真空氣相沈積設備沈積厚度為80nm的Al陰極。因此,製得OLED裝置。用於製造OLED裝置之所有材料均為藉由在10-6托下真空昇華而純化的材料。
OLED的在15,000nit下亮度自100%降低至97%所耗費之時間以及恆定電流顯示於下表2中。
比較例3:製備包括習知磷光主體材料之OLED裝置
以裝置實例2相同之方式製造OLED裝置,但使用化合物H3-3代替化合物H1-71用作發光層之主體。
OLED的在15,000nit下亮度自100%降低至97%所耗費之時間以及恆定電流顯示於下表2中。
本發明之有機電致發光裝置包括具有多種主體化合物及一種磷光摻雜劑之發光層。複數種主體化合物之至少一第一主體化合物具有含氮雜環連接基團鍵結於吲哚-咔唑、茚-咔唑、苯并呋喃-咔唑或苯并噻吩-咔唑殘基之咔唑的
氮原子的結構,且第二主體化合物具有咔唑-芳基-咔唑或咔唑-咔唑結構。檢驗到本發明之有機電致發光裝置具有相較於習知裝置顯著延長壽命之作用。
Claims (10)
- 一種有機電致發光裝置,其包括至少一個介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;所述主體包括多種主體化合物;所述多種主體化合物中之至少一種第一主體化合物由以下式1表示;且第二主體化合物由以下式2表示;
- 如申請專利範圍第1項所述之有機電致發光裝置,其中在式2中,L1表示下式18至式30中之一者:
- 如申請專利範圍第1項所述之有機電致發光裝置,其中在式1及式2中,R1至R8、A1、A2、L1以及X1至X16中之所述經取代之烷基、所述經取代之烯基、所述經取代之炔基、所述經取代之烷氧基、所述經取代之環烷基、所述經取代之三烷基矽烷基、所述經取代之二烷基芳基矽烷基、所述經取代之烷基二芳基矽烷基、所述經取代之三芳基矽烷基、所述經取代之單或二烷基胺基、所述經取代之單或二芳基胺基、所述經取代之烷基芳基胺基、所述經取代之(伸)芳基、所述經取代之雜芳基以及所述經取代之單環或多環(C3-C30)脂環族環或芳族環的所述取代基各自獨立地為選自由以下組成之群的至少一者: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、單或二(C1-C30)烷基胺基、單或二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基基、二(C1-C30)烷基基、(C1-C30)烷基(C6-C30)芳基基、(C6-C30)芳基(C1-C30)烷基以及(C1-C30)烷基(C6-C30)芳基。
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2016
- 2016-01-07 KR KR1020160002171A patent/KR20170001552A/ko unknown
- 2016-04-21 KR KR1020160048912A patent/KR102646953B1/ko active IP Right Grant
- 2016-05-13 EP EP16814586.0A patent/EP3313958B1/en active Active
- 2016-05-13 CN CN201680034175.1A patent/CN107771206B/zh active Active
- 2016-05-13 JP JP2017563341A patent/JP6735295B2/ja active Active
- 2016-05-13 EP EP19209591.7A patent/EP3636726B1/en active Active
- 2016-05-13 US US15/580,082 patent/US20180301636A1/en not_active Abandoned
- 2016-05-13 CN CN202110494913.3A patent/CN113206210A/zh active Pending
- 2016-06-07 TW TW105118037A patent/TWI699365B/zh active
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2021
- 2021-03-18 US US17/205,211 patent/US20210210699A1/en not_active Abandoned
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2023
- 2023-11-15 US US18/509,819 patent/US20240099132A1/en active Pending
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2024
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WO2015156587A1 (en) * | 2014-04-08 | 2015-10-15 | Rohm And Haas Electronic Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
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CN113206210A (zh) | 2021-08-03 |
US20240099132A1 (en) | 2024-03-21 |
EP3636726B1 (en) | 2021-07-14 |
KR20170001552A (ko) | 2017-01-04 |
JP2018520513A (ja) | 2018-07-26 |
KR102646953B1 (ko) | 2024-03-14 |
KR20170001563A (ko) | 2017-01-04 |
EP3313958A1 (en) | 2018-05-02 |
CN107771206B (zh) | 2021-05-28 |
CN107771206A (zh) | 2018-03-06 |
JP6735295B2 (ja) | 2020-08-05 |
TW201700479A (zh) | 2017-01-01 |
US20180301636A1 (en) | 2018-10-18 |
US20210210699A1 (en) | 2021-07-08 |
EP3313958B1 (en) | 2020-02-12 |
EP3636726A1 (en) | 2020-04-15 |
EP3313958A4 (en) | 2019-02-27 |
KR20240037908A (ko) | 2024-03-22 |
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