TWI653211B - 化合物及其有機電子裝置 - Google Patents
化合物及其有機電子裝置 Download PDFInfo
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- TWI653211B TWI653211B TW106126651A TW106126651A TWI653211B TW I653211 B TWI653211 B TW I653211B TW 106126651 A TW106126651 A TW 106126651A TW 106126651 A TW106126651 A TW 106126651A TW I653211 B TWI653211 B TW I653211B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
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- 239000010410 layer Substances 0.000 claims description 106
- 125000000524 functional group Chemical group 0.000 claims description 70
- -1 benzoanthracenyl Chemical class 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 238000002347 injection Methods 0.000 claims description 26
- 239000007924 injection Substances 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 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 13
- 239000000758 substrate Substances 0.000 claims description 13
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- 230000005540 biological transmission Effects 0.000 claims description 12
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
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- 125000000707 boryl group Chemical group B* 0.000 claims description 4
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
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- 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N thianaphthalene Natural products C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- QKHBRTOZTSOCKN-UHFFFAOYSA-N phenanthro[9,10-c]pyridazine Chemical group N1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 QKHBRTOZTSOCKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005498 phthalate group Chemical class 0.000 claims description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical group C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical group C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 1
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 claims 1
- UFQRGMNBFKKDSH-UHFFFAOYSA-N N1C=CC=CC2=C1C=CC=C2.C2=CC=CC=1C3=CC=CC=C3C3=CC=CC=C3C21 Chemical class N1C=CC=CC2=C1C=CC=C2.C2=CC=CC=1C3=CC=CC=C3C3=CC=CC=C3C21 UFQRGMNBFKKDSH-UHFFFAOYSA-N 0.000 claims 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
- ODSSEMUGTRVRIK-UHFFFAOYSA-N [1]benzothiolo[3,2-c]pyridazine Chemical class C1=NN=C2C3=CC=CC=C3SC2=C1 ODSSEMUGTRVRIK-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 230000004888 barrier function Effects 0.000 claims 1
- 150000001721 carbon Chemical class 0.000 claims 1
- 229940126543 compound 14 Drugs 0.000 claims 1
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- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 description 94
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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- 238000000434 field desorption mass spectrometry Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
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- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 2
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- JSTHREDTMPIBEX-UHFFFAOYSA-N pyrene-2,7-diamine Chemical class C1=C(N)C=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 JSTHREDTMPIBEX-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 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
- 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 1
- 150000003649 tritium Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
本發明是關於一種化合物及其有機裝置,該化合物可以下式(I)表示:
其中,a1和a2各自獨立為0至4的整數,a1和a2的總和不小於1;l1和l2各自獨立為0至3的整數;L1和L2各自獨立為一經取代或未經取代且環上碳數為6至60的亞芳基;b是0至4的整數;c是0至2的整數。
Description
本發明是關於一種新穎化合物以及一種使用其之有機電子裝置,尤指一種用於電子傳輸層的新穎化合物以及使用其之有機電子裝置。
隨著科技的進步,各種使用有機材料製成的有機電子裝置蓬勃發展,常見的有機電子裝置如有機發光二極體(organic light emitting device,OLED)、有機光電晶體(organic phototransistor)、有機光伏打電池(organic photovoltaic cell)和有機光偵測器(organic photodetector)。
OLED最初是由伊士曼柯達公司(Eastman Kodak)所發明並提出,伊士曼柯達公司的鄧青雲博士和Steven Van Slyke以真空蒸鍍法(vacuum evaporation method)於形成有有機芳香二元胺電洞傳輸層的透明氧化銦錫(indium tin oxide,ITO)玻璃上沉積一電子傳輸材料{例如三(8-羥基喹啉)鋁[tris(8-hydroxyquinoline)aluminum(III),簡稱為Alq3]};再於電子傳輸層上沉積一金屬電極,即可完成OLED的製作。OLED因兼具反應速率快、質輕、薄形化、廣視角、亮度高、對比高、無需設置背光源以及低耗能的優點,因此備受關注,但OLED仍具有低效率和壽命短的問題。
為了克服低效率的問題,其中一種改善方式為於陰極和陽極間設置中間層,請參閱圖1所示,改良的OLED依序設置有一基板11、一陽極12、一電洞注入層13(hole injection layer,HIL)、一電洞傳輸層14(hole
transport layer,HTL)、一發光層15(an emission layer,EL)、一電子傳輸層16(electron transport layer,ETL)、一電子注入層17(electron injection layer,EIL)和一陰極18。當於陽極12和陰極18施加一電壓時,由陽極12射出的電洞會穿過HIL和HTL並移動至EL,而由陰極18射出的電子會穿過EIL和ETL移動至EL,使電洞和電子在EL層重組成激子(exciton),當激子由激發態衰退返回基態時即可產生光線。
另一改善方式為改良OLED中ETL的材料,使電子傳輸材料展現出電洞阻擋能力,傳統的電子傳輸材料包括3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1"-三聯苯]-3,3"-二基]聯吡啶((3,3'-[5'-[3-(3-pyridinyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]bispyridine,TmPyPb)、1,3,5-三(1-苯基-1H-苯並咪唑-2-基)苯(1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene,TPBi)、三(2,4,6-三甲基-3-(3-吡啶基)苯基)硼烷(tris(2,4,6-trirmethyl-3-(pyridin-3-yl)phenyl)borane,3TPYMB)、1,3-聯(3,5-二吡啶-3-基-苯基)苯(1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene,BmPyPb)和9,10-聯(3-(3-吡啶基)苯基)蒽(9,10-bis(3-(pyridin-3-yl)phenyl)anthracene,DPyPA)。
然而,即使使用了所述電子傳輸材料,OLED的電流效率仍具有可改善的空間,因此,本發明提供了一種新穎的化合物以克服傳統低電流效率的問題。
本發明的目的為提供一種新穎化合物,其可用於有機電子裝置。
本發明的另一目的為提供一種使用該新穎化合物的有機電子裝置,藉此降低有機電子裝置之驅動電壓,並提升有機電子裝置的效率。
為達上述目的,本發明的新穎化合物具有式(I):
於式(I)中,a1和a2各自獨立為0至4的整數,a1和a2的總和不小於1;l1和l2各自獨立為0至3的整數;L1和L2各自獨立為一經取代或未經取代且環上碳數為6至60的亞芳基(arylene group);G1和G2各自獨立選自於由下列所構成的群組:環上碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷基、具有至少一官能基且碳數為2至40的烯基、具有至少一官能基且碳數為2至40的炔基、具有至少一官能基且環上碳數為3至60的環烷基、具有至少一官能基且環上碳數為3至60的雜環烷基、具有至少一官能基且碳數為1至40的烷氧基、具有至少一官能基且環上碳數為6至60的芳香基、具有至少一官能基且環上碳數為6至60的芳氧基、具有至少一官能基且碳數為1至40的矽烷基(alkylsilyl group)、具有至少一官能基且環上碳數為6至60的芳矽基(arylsilyl group)、具有至少一官能基且碳數為1至40的硼烷基(alkylboron)、具有至少一官能基且環上碳數為6至60的芳硼基(arylboron group)、具有至少一官能基且碳數為1至40的膦基(phosphine group)、具有至少一官能基且碳數為1至40的氧膦基(phosphine oxide group)、上述任一者之異構物及其氘化物;
其中,該至少一官能基是選自於由下列所構成的群組:氰基、硝基、三氟甲基(trifluoromethyl group)、氟基和氯基;b是0至4的整數;X是選自於由下列所構成的群組:氘原子、氟基、氯基、溴基、一未經取代且碳數為6至60的芳香基、一未經取代且碳數為1至12的烷基、一未經取代且碳數為2至12的烯基和一未經取代且碳數為2至12的炔基;c是0至2的整數;Y是選自於由下列所構成的群組:氘原子、一經取代或未經取代且環上碳數為6至60的芳香基和一經取代或未經取代且環上碳數為3至60的雜芳基。
前述連接有至少一特定基團(「L1-G1」或「L2-G2」)的化合物適合作為任合色光之OLED的電子傳輸層的材料,並可使所述化合物製成的OLED的具有較低的驅動電壓並可改善其電流效率以及外部量子效率(external quantum efficiency,EQE)。
較佳的,該特定基團僅連接於該化合物主結構的上半部或下半部。換句話說,於其中一實施例,a1是1而a2是0;於另一實施例,a1是0而a2是1。
較佳的,該特定基團((L1-G1)和(L2-G2))分別連接於該化合物主結構的下半部和上半部,但該化合物主結構的上半部僅連接一個所述特定基團,而該化合物主結構的下半部僅連接一個所述特定基團。也就是說,a1是1且a2也是1。
更佳的,該化合物可以下述任一結構式表示:
較佳的,所述G1和G2可以是環上碳數為3至60的雜芳基,係指G1和G2各自獨立選自於由下列所構成的群組:一經取代或未經取代的呋喃基(furyl group)、一經取代或未經取代的吡咯基(pyrrolyl group)、一經取代或未經取代的噻吩基(thiophenyl group)、一經取代或未經取代的咪唑基(imidazolyl group)、一經取代或未經取代的吡唑基(pyrazolyl group)、一經取代或未經取代的***基(triazolyl group)、一經取代或未經取代的四唑基(tetrazolyl group)、一經取代或未經取代的噁唑基(oxazolyl group)、一經取代或未經取代的異噁唑基(isoxazolyl group)、一經取代或未經取代的噻唑基(thiazolyl group)、一經取代或未經取代的異噻唑基(isothiazolyl group)、一經取代或未經取代的噁二唑基(oxadiazolyl group)、一經取代或未經取代的噻二唑基(thiadiazolyl group)、一經取代或未經取代的吡啶基(pyridyl group)、一經取代或未經取代的噠嗪基(pyridazinyl group)、一經取代或未經取代的嘧啶基(pyrimidinyl group)、一經取代或未經取代的吡嗪基(pyrazinyl group)、一經取代或未經取代的三嗪基(triazinyl group)、一經取代或未經取代的吲哚基(indolyl group)、一經取代或未經取代的異吲哚基(isoindolyl group)、一經取代或未經取代的苯並呋喃基(benzofuranyl group)、一經取代或未經取代的
異苯並呋喃基(isobenzofuranyl group)、一經取代或未經取代的苯並噻吩基(benzothiophenyl group)、一經取代或未經取代的異苯並噻吩基(isobenzothiophenyl group)、一經取代或未經取代的吲哚嗪基(indolizinyl group)、一經取代或未經取代的喹嗪基(quinolizinyl group)、一經取代或未經取代的喹啉基(quinolyl group)、一經取代或未經取代的異喹啉基(isoquinolyl group)、一經取代或未經取代的噌啉基(cinnolyl group)、一經取代或未經取代的酞嗪基(phthalazinyl group)、一經取代或未經取代的喹唑啉基(quinazolinyl group)、一經取代或未經取代的喹喔啉基(quinoxalinyl group)、一經取代或未經取代的苯並咪唑(benzimidazolyl group)、一經取代或未經取代的苯並噁唑基(benzoxazolyl group)、一經取代或未經取代的苯並噻唑基(benzothiazolyl group)、一經取代或未經取代的吲唑基(indazolyl group)、一經取代或未經取代的苯並三嗪基(benzotriazinyl group)、一經取代或未經取代的聯吡啶基(dipyridyl group)、一經取代或未經取代的苯並異噁唑基(benzisoxazolyl group)、一經取代或未經取代的苯並異噻唑基(benzisothiazolyl group)、一經取代或未經取代的二苯並呋喃基(dibenzofuranyl group)、一經取代或未經取代的二苯並噻吩基(dibenzothiophenyl group)、一經取代或未經取代的咔唑基(carbazolyl group)、一經取代或未經取代的二咔唑基(biscarbazolyl group)、一經取代或未經取代的香豆素基(coumarinyl group)、一經取代或未經取代的色烯基(chromenyl group)、一經取代或未經取代的菲基(phenanthridinyl group)、一經取代或未經取代的吖啶基(acridinyl group)、一經取代或未經取代的啡啉基(phenanthrolinyl group)、一經取代或未經取代的吩嗪基(phenazinyl group)、一經取代或未經取代的吩噻嗪基(phenothiazinyl group)、一經取代或未經取代的吩噁嗪基(phenoxazinyl group)、一經取代或未經取代的氮雜二苯並噻吩
基(azatriphenylenyl group)、一經取代或未經取代的二氮雜二苯並噻吩基(diazatriphenylenyl group)、一經取代或未經取代的呫噸基(xanthenyl group)、一經取代或未經取代的氮雜咔唑基(azacarbazolyl group)、一經取代或未經取代的氮雜苯並呋喃基(azadibenzofuranyl group)、一經取代或未經取代的氮雜苯並噻吩基(azadibenzothiophenyl group)、一經取代或未經取代的苯並呋喃苯並噻吩基(benzofuranobenzothiophenyl group)、一經取代或未經取代的苯並噻吩苯並噻吩基(benzothienobenzothiophenyl group)、一經取代或未經取代的二苯並呋喃萘基(dibenzofuranonaphthyl group)、一經取代或未經取代的二苯並噻吩萘基(dibenzothienonaphthyl group)、一經取代或未經取代的二萘噻吩噻吩苯基(dinaphthothienothiophenyl group)、一經取代或未經取代的二萘咔唑基(dinaphtho carbazolyl group)、一經取代或未經取代的二苯並氮雜基(dibenzo[b,f]azepin group)、一經取代或未經取代的三苯並氮雜基(tribenzo[b,d,f]azepin group)、一經取代或未經取代的二苯並氧雜基(dibenzo[b,f]oxepin group)、一經取代或未經取代的三苯並氧雜基(tribenzo[b,d,f]oxepin group)、上述任一者之異構物及其氘化物。
更佳的,所述G1和G2可以是各自獨立選自於由下列所構成的群組:一經取代或未經取代的吡啶基、一經取代或未經取代的噠嗪基、一經取代或未經取代的嘧啶基、一經取代或未經取代的吡嗪基、一經取代或未經取代的三嗪基、一經取代或未經取代的吲哚嗪基、一經取代或未經取代的喹嗪基、一經取代或未經取代的喹啉基、一經取代或未經取代的異喹啉基、一經取代或未經取代的酞嗪基、一經取代或未經取代的喹唑啉基、一經取代或未經取代的喹喔啉基、一經取代或未經取代的苯並咪唑基、一經取代或未經取代的吲唑基、一經取代或未經取代的喹喔啉基、一經取代或未經取代的苯並咪唑、一經取代或未經取代的吲唑基、一經取代或未經
取代的苯並三嗪基、一經取代或未經取代的聯吡啶基、一經取代或未經取代的吡咯基、一經取代或未經取代的咪唑基、一經取代或未經取代的吡唑基、一經取代或未經取代的***基、一經取代或未經取代的苯並吡咯基、一經取代或未經取代的苯並咪唑基、一經取代或未經取代的苯並***基和上述任一者之氘化物。
具體來說,G1和G2各自獨立選自於由下列所構成的群組:
其中,o是0至2的整數,m是0至3的整數,n是0至4的整數,p是0至5的整數;R1至R5各自獨立選自於由下列所構成的群組:氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12
的炔基、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至30的雜芳基、碳數為1至40的烷氧基、環上碳數為6至30的芳氧基、碳數為1至40的矽烷基、環上碳數為6至30的芳矽基、碳數為1至30的硼烷基、環上碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基。
較佳的,所述G1和G2可以是具有至少一官能基且環上碳數為6至60的芳香基,係指G1和G2各自獨立選自於由下列所構成的群組:具有至少一官能基的苯基、具有至少一官能基的聯苯基、具有至少一官能基的三聯苯基(terephenyl group)、具有至少一官能基的萘基、具有至少一官能基的菲基(phenanthryl group)、具有至少一官能基的蒽基(anthracenyl group)、具有至少一官能基的苯並蒽基(benzanthryl group)、具有至少一官能基的芴基(fluorenyl group)、具有至少一官能基的基(chrycenyl group)、具有至少一官能基的荧蒽基(fluoranthenyl group)及上述任一者的氘化物。
更佳的,所述G1和G2可以是具有至少一官能基且環上碳數為6至60的芳香基是選自於由具有至少一官能基的苯基和具有至少一官能基的聯苯基所構成的群組。
具體而言,所述G1和G2可以是具有至少一官能基且環上碳數為6至60的芳香基,係指G1和G2各自獨立選自於由下列所構成的群組:
其中,r是1至5的整數,s是0到4的整數,r和s的總和不大於5;其中,R1'選自於由下列所構成的群組:氘原子、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至30
的雜芳基、碳數為1至12的烷氧基、環上碳數為6至30的芳氧基、碳數為1至12的矽烷基、環上碳數為6至30的芳矽基、碳數為1至12的硼烷基和環上碳數為6至30的芳硼基。
較佳的,X是選自於由下列所構成的群組:氘原子、氟基、氯基、溴基、苯基、聯苯基、三聯苯基、萘基、菲基、蒽基、苯並蒽基、芴基、基、荧蒽基、氘化苯基、氘化聯苯基、氘化三聯苯基、氘化萘基、氘化菲基、氘化蒽基、氘化苯並蒽基、氘化芴基、氘化基和氘化荧蒽基。
更佳的,X是選自於由下列所構成的群組:氘原子、氟基、氯基、溴基、苯基、聯苯基、氘化苯基和氘化聯苯基。
較佳的,Y是選自於由下列所構成的群組:氘原子、未經取代的苯基、未經取代的聯苯基、未經取代的三聯苯基、未經取代的萘基、未經取代的菲基、未經取代的蒽基、未經取代的苯並蒽基、未經取代的芴基、未經取代的基、未經取代的荧蒽基、氘化苯基、氘化聯苯基、氘化三聯苯基、氘化萘基、氘化菲基、氘化蒽基、氘化苯並蒽基、氘化芴基、氘化基、氘化荧蒽基;未經取代的呋喃基、未經取代的吡咯基、未經取代的噻吩基、未經取代的咪唑基、未經取代的吡唑基、未經取代的***基、未經取代的四唑基、未經取代的噁唑基、未經取代的異噁唑基、未經取代的噻唑基、未經取代的異噻唑基、未經取代的噁二唑基、未經取代的噻二唑基、未經取代的吡啶基、未經取代的噠嗪基、未經取代的嘧啶基、未經取代的吡嗪基、未經取代的三嗪基、未經取代的吲哚基、未經取代的異吲哚基、未經取代的苯並呋喃基、未經取代的異苯並呋喃基、未經取代的苯並噻吩基、未經取代的異苯並噻吩基、未經取代的吲哚嗪基、未經取代的喹嗪基、未經取代的喹啉基、未經取代的異喹啉基、未經取代的噌啉基、未經取代的酞嗪基、未經取代的喹唑啉基、未經取代的喹喔啉基、未經取
代的苯並咪唑、未經取代的苯並噁唑基、未經取代的苯並噻唑基、未經取代的吲唑基、未經取代的苯並異噁唑基、未經取代的苯並異噻唑基、未經取代的二苯並呋喃基、未經取代的二苯並噻吩基、未經取代的咔唑基、未經取代的二咔唑基、未經取代的香豆素基、未經取代的色烯基、未經取代的菲基、未經取代的吖啶基、未經取代的啡啉基、未經取代的吩嗪基、未經取代的吩噻嗪基、未經取代的吩噁嗪基、未經取代的氮雜三亞苯基、二氮雜三亞苯基、未經取代的呫噸基、未經取代的氮雜咔唑基、未經取代的氮雜苯並呋喃基、未經取代的氮雜苯並噻吩基、未經取代的苯並呋喃苯並噻吩基、未經取代的苯並噻吩苯並噻吩基、未經取代的二苯並呋喃萘基、未經取代的二苯並噻吩萘基、未經取代的二萘噻吩噻吩苯基、未經取代的二萘噻吩噻吩苯基、未經取代的二萘咔唑基、未經取代的二苯並氮雜基、未經取代的三苯並氮雜基、未經取代的二苯並氧雜基、未經取代的三苯並氧雜基;具有至少一官能基的苯基、具有至少一官能基的聯苯基、具有至少一官能基的三聯苯基、具有至少一官能基的萘基、具有至少一官能基的菲基、具有至少一官能基的蒽基、具有至少一官能基的苯並蒽基、未具有至少一官能基的芴基、具有至少一官能基的基、具有至少一官能基的荧蒽基;其中,該至少一官能基是選自於由下列所構成的群組:氰基、硝基、三氟甲基、氟基和氯基。
更佳的,Y是選自於由下列所構成的群組:未經取代的苯基、未經取代的聯苯基、具有至少一官能基的苯基、具有至少一官能基的聯苯基;其中,該至少一官能基是選自於由下列所構成的群組:氰基、硝基、三氟甲基、氟基和氯基。
較佳的,L1和L2各自獨立選自於由下列所構成的群組:
更佳的,L1和L2各自獨立選自於由下列所構成的群組:
舉例來說,當該化合物主結構的下半部連接有該特定基團(L1-G1)時,其結構可如下所示:
或者,當該化合物主結構的上半部連接有該特定基團(L2-G2)時,其結構可如下所示:
又或者,當該化合物主結構的下半部連接有該特定基團(L1-G1)且上半部連接有該特定基團(L2-G2)時,其結構可如下所示:
另一方面,當該化合物主結構的下半部連接有該特定基團(L1-G1)且連接有Y時,其結構可如下所示:
又另一方面,當該化合物主結構的下半部連接有該特定基團(L1-G1)且連接有X時,其結構可如下所示:
本發明另提供一有機電子裝置,其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層,該有機層包括所述化合物。
較佳的,該有機電子裝置為一有機發光二極體。更佳的,該新穎化合物可被使用於該電子傳輸層或電洞阻擋層。
具體而言,該有機發光二極體包括一電洞注入層、一電洞傳輸層、一發光層、一電子傳輸層和一電子注入層;該電洞注入層形成於該第一電極上;該電洞傳輸層形成於該電洞注入層上;該發光層形成於該電洞傳輸層上;該電子傳輸層形成於該發光層上;該電子注入層形成於該電子傳輸層和該第二電極之間。
於其中一實施例,該有機層為該電子傳輸層,即該電子傳輸層包含有所述新穎化合物。
較佳的,該電洞注入層可以為一雙層結構,即該OLED具有一第一電洞注入層和一第二電洞注入層,第一電洞注入層和第二電洞注入層設置於第一電極和電洞傳輸層之間。
相同的,該電洞傳輸層亦可以為一雙層結構,即該OLED具有一第一電洞傳輸層和一第二電洞傳輸層,第一電洞傳輸層和第二電洞傳輸層設置於電洞注入層的雙層結構與發光層之間。
較佳的,該電子傳輸層是由該新穎化合物所製成,本發明的OLED相較於商業上的OLED具有較佳的電流效率,其中商業上的OLED使用的化合物如2-{4-[9,10-二(2-萘基)-2-蒽基]苯基}-1-苯基-1H-苯並[d]咪唑(2-[4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl]-1-phenyl-1H-benzo[d]imidazole)、二(2-甲基-8-羥基喹啉)(p-苯基苯酚)鋁(bis(2-methyl-8-quinolinolato)(p-phenylphenolato)aluminum)或2-(4-聯苯
基)-5-(4-叔丁苯基)-1,3,4-噁二唑(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole),PBD)。
較佳的,該OLED包括一電洞阻擋層,該電洞阻擋層形成於電子傳輸層和發光層之間,可防止電洞由發光層移動至電子傳輸層,所述電洞阻擋層可由前述化合物、2,9-二甲基-4,7-二苯基-1,10-鄰二氮雜菲(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline,BCP)或2,3,5,6-四甲基苯基-1,4-鄰苯二甲醯亞胺(2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide),TMPP)所形成,但並不僅限於此。
較佳的,該OLED包括一電子阻擋層,該電子阻擋層形成於電洞傳輸層和發光層之間,可防止電子由發光層移動至電洞傳輸層,所述電子阻擋層可由9,9’-(1,1’-聯苯基)-4,4’-二基二-9H-咔唑(9,9'-(1,1'-biphenyl)-4,4'-diylbis-9H-carbazole,CBP)或4,4',4"-三(N-咔唑基)三苯胺(4,4',4"-tri(N-carbazolyl)-triphenylamine,TCTA)所形成,但並不僅限於此。
當OLED設置有電洞阻擋層和/或電子阻擋層時,本發明的OLED相較於傳統的OLED具有較高的發光效率。
所述第一和第二電洞傳輸層可由但不限於N 1 ,N 1’ -(聯苯-4,4’-二基)聯(N 1 -(1-萘基))-N 4 ,N 4' -二苯基苯-1,4-二胺(N 1 ,N 1’ -(biphenyl-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4’ -diphenylbenzene-1,4-diamine))或N 4 ,N 4' -二(萘-1-基)-N 4 ,N 4’ -二苯聯苯基-4,4'-二胺(N 4 ,N 4' -di(naphthalen-1-yl)-N 4 ,N 4’ -diphenylbiphenyl-4,4'-diamine,NPB)所製成。
所述第一和第二電洞注入層可由但不限於聚苯胺或聚乙烯基二氧噻吩(polyethylenedioxythiophene)所製成。
所述發光層可由一發光材料製成,該發光材料包括一主發光體(host)和一摻雜物(dopant),發光材料中主發光體的材料可以是但不限於9-[4-(1-萘基)苯基]-10-(2-萘基)蒽(9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl)anthracene)。
針對紅光OLED,發光層中的摻雜物可以為具有苝(perylene)配位基、熒蒽(fluoranthene)配位基或二茚並(periflanthene)配位基的二價銥有機金屬化合物,但並不僅限於此。針對綠光OLED,發光層中的摻雜物可以為二氨基芴(diaminofluorenes)、蒽二胺(diaminoanthracenes)或具有苯基吡啶(phenylpyridine)配位基的二價銥有機金屬化合物,但並不僅限於此。針對藍光OLED,發光層中的摻雜物可以為二氨基芴、蒽二胺、芘二胺(diaminopyrenes)或具有苯基吡啶配位基的二價銥有機金屬化合物,但並不僅限於此。藉由不同的主發光體材料,OLED可產生紅光、綠光或藍光的光線。
所述電子注入層可以一電子注入材料製成,例如8-氧代萘-1-基鋰((8-oxidonaphthalen-1-yl)lithium(II)),但不限於此。
所述第一電極可以為氧化銦錫電極(indium-doped tin oxide electrode),但並不僅限於此。
所述第二電極的功函數(work function)低於第一電極的功函數。因此,第二電極可以是但不侷限於鋁電極、銦電極或鎂電極。
本發明的其他目的、功效和技術特徵,會以圖式、實施例和比較例進行更詳細的說明。
11‧‧‧基板
12‧‧‧陽極
13‧‧‧電洞注入層
14‧‧‧電洞傳輸層
15‧‧‧發光層
16‧‧‧電子傳輸層
17‧‧‧電子注入層
18‧‧‧陰極
圖1為OLED的側視剖面圖。
圖2至26分別為化合物1至8、13、14、17至20、25至31以及比較例1至4中使用材料的氫核磁共振光譜圖。
以下列舉數種實施例作為例示說明本發明的化合物及其有機電子裝置的實施方式,以突顯本發明相較於現有技術的差異;熟習此技藝者可經由本說明書的內容輕易了解本發明所能達成的優點與功效,並且於不悖離本發明之精神下進行各種修飾與變更,以施行或應用本發明的內容。
中間物A的製備
中間物A1至A7係用於製備一種新穎化合物,中間物A1至A7可購買自現有商品或是藉由下述步驟合成,中間物A1至A7的詳細化學結構列於下表1中。
中間物A1
中間物A1(CAS No.2222-33-5)購自Sigma-Aldrich。
中間物A2的合成
中間物A2可藉由下述合成機制A1中的步驟進行合成。
混合10-溴-5H-二苯並[a,d]環庚烯-5-酮(10-bromo-5H-dibenzo[a,d]cyclohepten-5-one)(CAS No.17044-50-7)(1.0eq)、苯基硼酸(1.05eq,CAS 98-80-6)、醋酸鈀(Pd(OAc)2)(0.012eq)、三苯基磷(triphenylphosphine,PPh3)(0.048eq)和碳酸鉀(2.0eq、3M)於甲苯/乙醇(v/v=10:1)中,並於90℃的溫度下加熱16小時,反應完成後於真空環境去除揮發性物質並以二氯甲烷萃取溶液,合併有機相後以飽和食鹽水洗淨並以硫酸鎂乾燥,接著在減壓的環境下濃縮並在管柱層析儀中純化,最後獲得橘色油相,產率為97%。該橘色油相產物經場脫附質譜(field desorption mass spectroscopy,FD-MS)分析確定為中間物A2。FD-MS分析結果:C21H14O,理論值282.34,檢測值282.34。
中間物A3的合成
中間物A3可藉由類似於合成中間物A2的步驟合成,其差異在於:起始物苯基硼酸以4-氟苯硼酸(4-fluorobenzeneboronic acid)(CAS No.1765-93-1)代替,產率為96%,以FD-MS分析:C21H13FO,理論值為300.33,檢測值為300.33。
中間物A4的合成
中間物A4可藉由類似於合成中間物A2的步驟合成,其差異在於:起始物10-溴-5H-二苯並[a,d]環庚烯-5-酮以2-溴二苯並庚酮(2-bromodibenzoheptenone)(CAS No.124853-22-1)代替,產率為94%,以FD-MS分析:C21H14O,理論值為282.34,檢測值為282.34。
中間物A5的合成
中間物A5可藉由下述合成機制A2中的步驟進行合成,詳細結果列於下表2中。
步驟1:合成中間物A5-1
將1當量的二甲基(3-氧代-1,3-二氫異苯並呋喃-1-基)磷酸酯(dimethyl(3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate)(CAS No.61260-15-9)和0.7當量的4-氟苯甲醛(CAS No.459-57-4)於2.5M的THF中混合,緩慢加入10當量的三乙胺(triethylamine,NEt3)並於室溫下攪拌24小時,待反應完成後,該混合溶液於低壓環境下濃縮,再以水和甲醇沖洗並過濾獲得黃色固體產物即為中間物A5-1。
步驟2:合成中間物A5-2
將中間物A5-1(1.0eq)和紅磷(4.5eq)溶於氫碘酸(8.5eq)中並加熱回流24小時,待反應完成後,將該熱反應溶液傾倒於冰塊上並過濾,收集沉澱物後以水沖洗並以氫氧化銨加熱回流一小時,接著,將該熱反應溶液過濾並以氫氯酸酸化後可獲得中間物A5-2,且無需進一步純化即可用於下步驟。
步驟3:合成中間物A5-3
將中間物A5-2(1.0eq)溶於多磷酸(polyphosphoric acid,PPA)中並於70℃下攪拌6小時,待反應溶液冷卻至室溫後倒於冰水中,並以氫氧化鈉鹼化再以醋酸乙酯萃取,殘餘液於管柱層析後純化或得殘餘物,藉由甲苯使該殘餘物再結晶最後獲得白色固體產物。
步驟4:合成中間物A5-4
在一圓底燒瓶中加入混合有中間物A5-3(1.0eq)、N-溴代丁二烯亞胺(2.0eq)和過氯化苯(1.0%eq)的且體積為中間物A5-3五倍的四氯化碳溶液,使該溶液於暗室中回流20小時,該溶液的顏色會轉為亮紅色,接著,以水(2x1500ml)和3%的碳酸氫鈉水溶液(2x1500ml)沖洗,分離有機相後於低壓環境下去除溶劑最後並獲得214.0g不可溶的米白色固體中間物A5-4,且不需純化即可進行下一步驟。
步驟5:合成中間物A5-5
126.0g的中間物A5-4溶於378毫升的DMSO中,並於70℃下攪拌3小時,待冷卻至室溫後,將反應溶液倒入冰水中並攪拌過濾,使白色的過濾物以水沖洗並乾燥,最後獲得淡黃色產物。
中間物A6和A7的合成
中間物A6和A7是以類似於合成中間物A5的步驟所合成,其差異在於:起使物4-氟苯甲醛依序以4-溴苯甲醛和3-溴苯甲醛代替,中間物A6和A7皆以與前述類似的方法進行分析,詳細結果列於表2中。
中間物B的製備
中間物B1至B3係用於製備一種新穎化合物,其是購自於Sigma-Aldrich,詳細化學結構式列於表3中。
中間物C的合成
中間物C1至C13係以下述合成機制C1中的步驟進行合成。具體而言,中間物C1、C3、C9、C11和C12是由合成機制C1中的步驟1和步驟2所合成;中間物C2、C4至C8和C10是由合成機制C1中的步驟1和步驟2所合成,並且另經由合成機制C1中的步驟3進行修飾,中間物C1至C13的產率和FD-MS的分析結果列於表4中。
步驟1:中間物C-1的合成
將溶有1當量鎂和125毫升的THF置於200毫升的三頸燒瓶中,在減壓環境下以旋轉泵攪拌0.5小時,以氮氣將5.0毫升的***和1滴的二溴乙烷注入三頸燒瓶中形成一混合液;將中間物B(1.0eq)緩慢滴入混合液中且維持混合液處於回流狀態,當滴加完成後,將反應溶液於40℃下加熱3小時以形成格氏試劑(Grignard reagent)。待格氏試劑冷卻至室溫後,將前述中間物A(0.7eq)於0℃的環境下分成三部分加入三頸燒瓶中,再於室溫下攪拌12小時。當反應完成後,以水洗滌反應溶液,並以醋酸乙酯萃取水相溶液,接著合併萃取溶液和有機相以飽和食鹽水洗淨並以硫酸鎂乾燥。乾燥後,抽氣過濾該反應溶液,使濾液濃縮形成一淡黃色固體粉末,即為「中間物C-1」。
步驟2:中間物C-2的合成
將10克的中間物C-1溶於30毫升的PPA中並於65℃的溫度下攪拌6小時,待冷卻後,將溶液倒入冰水中並以氫氧化鈉鹼化再以醋酸乙酯萃取,接著使有機相以飽和食鹽水洗淨並乾燥濃縮,並在減壓環境下以旋轉泵去除溶劑,再使剩餘物經由管柱層析獲得中間物C-2。
步驟3:中間物C的合成
使中間物C-2(1.0eq)、雙聯頻哪醇硼酸酯(bis(pinacolato)diboron)(1.2eq)、三(二亞苄基丙酮)二鈀(tris(dibenzylideneacetone)dipalladium(0),Pd2(dba)3)(0.015eq)、三環己基磷四氟硼酸鹽(tricyclohexylphosphine tetrafluoroborate,P(Cy)3HBF4)(0.06eq)和乙酸鉀(3.0eq)溶於1,4-二噁烷(0.3M)中並在氮氣環境下於110℃加熱8小時,待冷卻至室溫後,在減壓的環境下去除溶劑,並使殘餘液以管柱層析進行純化,最後獲得淡黃色的固體。
中間物C13的合成
中間物C13是用以合成新穎化合物,中間物C13是以合成機制C2的步驟所合成。
將1當量的2,4-二氯-6-苯基嘧啶(CAS No.26032-72-4)、0.012當量的混合2,4-二氯-6-苯基嘧啶(2,4-dichloro-6-phenyl-pyrimidine)(CAS No.26032-72-4)(1.0eq)、1.05當量的中間物C2、四(三苯基膦)鈀(Pd(PPh3)4)(0.012eq)和碳酸鈉(2.0eq、3M)於THF(0.3M)中,並加熱至60℃反應16小時,反應完成後,於真空環境下去除揮發性物質,並以二氯甲烷萃取溶液,合併有機相後以飽和食鹽水洗滌並以硫酸鈉乾燥,再於低壓狀態以管柱層析下濃縮純化產物溶液,最後獲得中間物C13,中間物C13的產率為62%,FD-MS分析為C37H23ClN2,理論值為531.04,測量值為531.04。
中間物D的製備
中間物D係用於製備一種新穎化合物,中間物D1至D25的詳細化學結構列於表5中,其中,中間物D1、D4、D5、D9至D17、D20和D21是購買自Sigma-Aldrich。
中間物D2的合成
中間物D2是藉由下述合成機制D1的所合成。
將125毫升溶有鎂(1.0eq)的THF置於200毫升的三頸燒瓶中,在減壓環境下以旋轉泵攪拌0.5小時,將氘代溴苯-5d(3.0eq)緩慢滴入三頸燒瓶中形成一混合液,接著將該混合液加熱至40℃反應3小時以形成格氏試劑,待格氏試劑冷卻至室溫後,於0℃的溫度下將1,3,5-三氯-2,4,6-三氮雜苯(1.0eq)分成三部分加入格式試劑中,在於室溫下攪拌12小時。當反應完成後,以水洗滌反應溶液並以醋酸乙酯萃取水相,再將萃取相和有機相合併以飽和食鹽水沖洗,最後以硫酸鎂乾燥,於乾燥後以抽氣過濾濃縮獲得黃色固體粉末,即為中間物D2,產率為66%。經FD-MS分析確定,該固體產
物即為中間物D2。FD-MS分析結果:C15H10ClN3,理論值277.7,檢測值為277.7。
中間物D3的合成
中間物D3係以類似於合成中間物D2的步驟所合成,其差異在於:起使物氘代溴苯-5d以3-溴聯苯(3-bromobiphenyl)(CAS No.2113-57-7)代替,中間物D3的產率為68%。經FD-MS分析確定,該產物即為中間物D3。FD-MS分析結果:C27H18ClN3,理論值419.90,檢測值為419.90。
中間物D6和D7的合成
中間物D6和D7是藉由下述合成機制D2的所合成。
混合2,4-二氯-6-苯基嘧啶(2,4-dichloro-6-phenyl-pyrimidine)(CAS No.26032-72-4)(1.0eq)、苯基硼酸(1.05eq、CAS No.98-80-6)、Pd(PPh3)4(0.012eq)和碳酸鈉(2.0eq、3M)於THF(0.3M)中,並加熱至60℃反應16小時,反應完成後,於真空環境下去除揮發性物質,並以二氯甲烷萃取溶液,合併有機相後以飽和食鹽水洗滌並以硫酸鈉乾燥,再於低壓狀態以管柱層析下濃縮純化產物溶液,最後獲得中間物D6和D7,中間物D6和D7的產率和FD-MS分析結果列於表6中。
表6:合成中間物D6和D7使用的硼酸化學結構、中間物D6和D7的產率以及以FD-MS分析而得的分子式與質量。
中間物D8的合成
中間物D8是藉由下述合成機制D3的所合成。
混合2,4-二氯喹唑啉(2,4-dichloroquinazoline)(1.0eq、CAS No.607-68-1)、4-氰基苯硼酸(4-cyanophenylboronic acid)(1.05eq、CAS No.126747-14-6)、Pd(PPh3)4(0.012eq)和碳酸鈉(2.0eq、3M)於甲苯(0.3M)中,加熱至90℃反應16小時,反應完成後,於真空環境下去除揮發性物質,並以二氯甲烷萃取剩餘溶液,合併有機相後以飽和食鹽水洗滌並以硫酸鈉乾燥,接著使產物溶液以管柱層析純化獲得中間物D8,產率為83%。FD-MS分析結果:C18H8ClN3,理論值265.70,檢測值為265.70。
中間物D18和D19的合成
中間物D18和D19是用以合成新穎化合物,中間物D18和D19是根據合成機制D4的步驟合成。
將2,4,6-三氯嘧啶(2,4,6-trichloropyrimidine)(CAS No.3764-01-0)(1.0eq)、硼酸(1.05eq)、Pd(PPh3)4(0.012eq)和碳酸鈉(2.0eq,3M)於0.3M的THF中混合,並於60℃下加熱16小時,反應完成後於真空環境下去除揮發物,並以二氯甲烷萃取反應溶液,將萃取後的有機相合併後以鹽水洗滌再以硫酸鈉乾燥,將粗產物於低壓環境下濃縮再以管柱層析純化獲得中間物D18和D19,以FD-MS測得的結果列於表7。
新穎化合物的合成
各中間物C1至C13可分別與任一中間物D1至D25反應合成出新穎化合物,新穎化合物可藉由下述合成機制I-A或合成機制I-B中的步驟進行合成。合成機制I-A或合成機制I-B中,「中間物C」係選自於表4中包括中間物C1至C13的群組;「中間物Dn」係選自於表5中包括中間物D1至D25的群組,所述化合物是以下述方法A或方法B所合成並列於表8中。
方法A
中間物C(1.0eq)、中間物Dn(2.1eq)、醋酸鈀(0.01eq)、2-(二環己基磷基)聯苯[dicyclohexylphosphine(2-biphenyl),P(Cy)2(2-biPh)](0.04eq)、甲苯/乙醇(0.5M,v/v=10/1)和3.0M的碳酸鉀水溶液,在氮氣環境下於100℃的溫度攪拌12小時,待反應完成後,於產物溶液中加入水和甲苯,以溶劑萃取後使用硫酸鎂乾燥,接著,於低壓環境下去除有機相的溶劑,再以管柱層析純化產物溶液,以甲苯再結晶後即可獲得白色固體,即為新穎化合物。
方法B
中間物C(1.0eq)、中間物Dn(2.1eq)、三(二亞苄基丙酮)二鈀(Tris(dibenzylideneacetone)dipalladium,Pd2(dba)3)、2-(二環己基磷基)聯苯[dicyclohcxylphosphine(2-biphenyl),P(Cy)2(2-biPh)](0.04eq)、甲苯/乙醇(0.5M,v/v=10/1)和3.0M的碳酸鉀水溶液,在氮氣環境下於100℃的溫度攪拌12小時,待反應完成後,於產物溶液中加入水和甲苯,以溶劑萃取後使用硫酸鎂乾燥,接著,於低壓環境下去除有機相的溶劑,再以管柱層析純化產物溶液,以甲苯再結晶後即可獲得白色固體,即為新穎化合物。
化合物1至31的修飾
除了前述化合物1至31之外,所屬技術領域具有通常知識者可更替不同的中間物C和反應物D,並以類似於合成機制I-A或合成機制I-B的合成路徑合成出其他新穎化合物。
OLED裝置的製備
將塗佈有1500Å厚ITO層的玻璃基板(以下簡稱為ITO基板)置於含有洗潔劑(廠牌:Fischer Co.)的蒸餾水(以Millipore Co.公司的濾器過濾二次而得的蒸餾水)中,並以超音波震盪30分鐘;更換蒸餾水後再以超音波震盪10分鐘以洗淨ITO基板,並重複上述洗淨步驟一次;洗淨後,將前述玻璃基板以異丙醇、丙酮和甲醇以超音波震盪洗淨,並使之乾燥;接著,將玻璃基板置於電漿表面清潔機內,並以氧電漿清潔玻璃基板5分鐘,再將清潔後的玻璃基板置於真空蒸鍍機內。
之後,將真空蒸鍍機的真空度維持在1x10-6torr至3x10-7torr,並於ITO基板上依序沉積各種有機材料和金屬材料,並獲得實施例和比較例的OLED裝置。於此,該ITO基板上係依序沉積有第一電洞注入層(HIL-1)、第二電洞注入層(HIL-2)、第一電洞傳輸層(HTL-1)、第二電洞傳輸層(HTL-2)、藍/綠/紅發光層(BEL/GEL/REL)、電子傳輸層(ETL)、電子注入層(EIL)和陰極(Cthd)。
在上述OLED裝置的各層中,HAT是用於形成HI-1和HID;HI-2是用於形成HI-2;HT-1和HT-2是用於形成HTL-1和HTL-2;實施例的新穎化合物和比較例的化合物是用於形成ETL;Liq是用於形成ETD和EIL;
RH/GH/BH分別為形成REL/GEL/BEL的主要材料;RD/GD/BD可作為REL/GEL/BEL的摻雜物,上述各化合物的詳細化學結構式列於表9。
實施例的OLED裝置和比較例的OLED裝置的主要差異為,實施例的OELD裝置中ETL是以前述表8中的新穎化合物所製成;具體而言,實施例1至10和比較例1至4所使用的化合物列於表10。
為了製備紅光、綠光和藍光的OLED裝置,本發明將複數有機層設置於ITO基板上,其中,紅光、綠光和藍光的OLED裝置中各有機層設置的順序、材料和厚度分別列於表11至13中。
OLED裝置的效能
為了評估OLED裝置的效能,分別將紅光、綠光和藍光的OLED裝置連接於電源供應器(廠牌:Keithley;型號:2400),並以PR650的光度計檢測,所測得之色度以為國際照明委員會(Commission Internationale de L’Eclairage 1931,CIE)制定的色度座標[color coordinate(x,y)]示之,檢測結果列於下表14中。其中,藍光和紅光的OLED裝置是在1000尼特(1nit=1cd/m2)的亮度下檢測;綠光的OLED裝置是在3000尼特的亮度下檢測。
如表14所示,本發明採用新穎化合物作為電子傳輸層的原料,可有效降低紅光、綠光或藍光OLED的驅動電壓並改善電流效率以及外部量子效率。
藉由比較實施例1至5和比較例1或者比較實施例6至9和比較例2至4可得知,當化合物主結構的上半部或下半部只連接有一特定基團(L-G)時,其可作為任何色光之OLED的電子傳輸層,並可使包含有該化合物的OLED具有較低的驅動電壓以及較佳的電流效率以及外部量子效率。
Claims (14)
- 一種化合物,其係如下列式(I-I)至式(I-VIII)所表示:l1和l2各自獨立為0至3的整數;L1和L2各自獨立為一經取代或未經取代且碳數為6至60的亞芳基;G1和G2各自獨立選自於由下列所構成的群組:經取代或未經取代且碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷基、具有至少一官能基且碳數為2至40的烯基、具有至少一官能基且碳數為2至40的炔基、具有至少一官能基且環上碳數為3至60的環烷基、具有至少一官能基且環上碳數為3至60的雜環烷基、具有至少一官能基且碳數為1至40的烷氧基、具有至少一官能基且環上碳數為6至60的芳香基、上述任一者之異構物及其氘化物;其中,該至少一官能基是選自於由下列所構成的群組:氰基、硝基、三氟甲基、氟基和氯基;b是0至4的整數;X是選自於由下列所構成的群組:氘原子、氟基、氯基、溴基、一經氘取代且碳數為6至60的芳香基、一未經取代且碳數為6至60的芳香基、一未經取代且碳數為1至12的烷基、一未經取代且碳數為2至12的烯基和一未經取代且碳數為2至12的炔基;該經氘取代且碳數為6至60的芳香基是選自於由下列所構成的群組:氘化苯基、氘化聯苯基、氘化三聯苯基、氘化萘基、氘化菲基、氘化蒽基、氘化苯並蒽基、氘化芴基、氘化基和氘化荧蒽基;c是0至2的整數;Y是選自於由下列所構成的群組:氘原子、一經取代或未經取代且環上碳數為6至60的芳香基和一經取代或未經取代且環上碳數為3至60的雜芳基。
- 如請求項1所述之化合物,其中該G1和G2是環上碳數為3至60的雜芳基,G1和G2各自獨立選自於由下列所構成的群組:一經取代或未經取代的呋喃基、一經取代或未經取代的吡咯基、一經取代或未經取代的噻吩基、一經取代或未經取代的咪唑基、一經取代或未經取代的吡唑基、一經取代或未經取代的***基、一經取代或未經取代的四唑基、一經取代或未經取代的噁唑基、一經取代或未經取代的異噁唑基、一經取代或未經取代的噻唑基、一經取代或未經取代的異噻唑基、一經取代或未經取代的噁二唑基、一經取代或未經取代的噻二唑基、一經取代或未經取代的吡啶基、一經取代或未經取代的噠嗪基、一經取代或未經取代的嘧啶基、一經取代或未經取代的吡嗪基、一經取代或未經取代的三嗪基、一經取代或未經取代的吲哚基、一經取代或未經取代的異吲哚基、一經取代或未經取代的苯並呋喃基、一經取代或未經取代的異苯並呋喃基、一經取代或未經取代的苯並噻吩基、一經取代或未經取代的異苯並噻吩基、一經取代或未經取代的吲哚嗪基、一經取代或未經取代的喹嗪基、一經取代或未經取代的喹啉基、一經取代或未經取代的異喹啉基、一經取代或未經取代的噌啉基、一經取代或未經取代的酞嗪基、一經取代或未經取代的喹唑啉基、一經取代或未經取代的喹喔啉基、一經取代或未經取代的苯並咪唑、一經取代或未經取代的苯並噁唑基、一經取代或未經取代的苯並噻唑基、一經取代或未經取代的吲唑基、一經取代或未經取代的苯並三嗪基、一經取代或未經取代的聯吡啶基、一經取代或未經取代的苯並異噁唑基、一經取代或未經取代的苯並異噻唑基、一經取代或未經取代的二苯並呋喃基、一經取代或未經取代的二苯並噻吩基、一經取代或未經取代的咔唑基、一經取代或未經取代的二咔唑基、一經取代或未經取代的香豆素基、一經取代或未經取代的色烯基、一經取代或未經取代的菲基、一經取代或未經取代的吖啶基、一經取代或未經取代的啡啉基、一經取代或未經取代的吩嗪基、一經取代或未經取代的吩噻嗪基、一經取代或未經取代的吩噁嗪基、一經取代或未經取代的氮雜二苯並噻吩基、一經取代或未經取代的二氮雜二苯並噻吩基、一經取代或未經取代的呫噸基、一經取代或未經取代的氮雜咔唑基、一經取代或未經取代的氮雜苯並呋喃基、一經取代或未經取代的氮雜苯並噻吩基、一經取代或未經取代的苯並呋喃苯並噻吩基、一經取代或未經取代的苯並噻吩苯並噻吩基、一經取代或未經取代的二苯並呋喃萘基、一經取代或未經取代的二苯並噻吩萘基、一經取代或未經取代的二萘噻吩噻吩苯基、一經取代或未經取代的二萘咔唑基、一經取代或未經取代的二苯並氮雜基、一經取代或未經取代的三苯並氮雜基、一經取代或未經取代的二苯並氧雜基、一經取代或未經取代的三苯並氧雜基、上述任一者之異構物及其氘化物。
- 如請求項1所述之化合物,其中G1和G2是選自於由下列所構成的群組: 其中,o是0至2的整數,m是0至3的整數,n是0至4的整數,p是0至5的整數;R1至R5各自獨立選自於由下列所構成的群組:氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至30的雜芳基、碳數為1至40的烷氧基、環上碳數為6至30的芳氧基、碳數為1至40的矽烷基、環上碳數為6至30的芳矽基、碳數為1至30的硼烷基、環上碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基。
- 如請求項1所述之化合物,其中該G1和G2是具有至少一官能基且環上碳數為6至60的芳香基,該G1和G2各自獨立選自於由下列所構成的群組:具有至少一官能基的苯基、具有至少一官能基的聯苯基、具有至少一官能基的三聯苯基、具有至少一官能基的萘基、具有至少一官能基的菲基、具有至少一官能基的蒽基、具有至少一官能基的苯並蒽基、具有至少一官能基的芴基、具有至少一官能基的基、具有至少一官能基的荧蒽基及上述任一者的氘化物。
- 如請求項1所述之化合物,其中G1和G2可以是具有至少一官能基且環上碳數為6至60的芳香基,G1和G2各自獨立選自於由下列所構成的群組:r是1至5的整數,s是0到4的整數,r和s的總和不大於5;R1'選自於由下列所構成的群組:氘原子、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至30的雜芳基、碳數為1至12的烷氧基、環上碳數為6至30的芳氧基、碳數為1至12的矽烷基、環上碳數為6至30的芳矽基、碳數為1至12的硼烷基和環上碳數為6至30的芳硼基。
- 如請求項1所述之化合物,其中X是選自於由下列所構成的群組:氘原子、氟基、氯基、溴基、苯基、聯苯基、三聯苯基、萘基、菲基、蒽基、苯並蒽基、芴基、基、荧蒽基、氘化苯基、氘化聯苯基、氘化三聯苯基、氘化萘基、氘化菲基、氘化蒽基、氘化苯並蒽基、氘化芴基、氘化基和氘化荧蒽基。
- 如請求項1所述之化合物,其中Y是選自於由下列所構成的群組:氘原子、未經取代的苯基、未經取代的聯苯基、未經取代的三聯苯基、未經取代的萘基、未經取代的菲基、未經取代的蒽基、未經取代的苯並蒽基、未經取代的芴基、未經取代的基、未經取代的荧蒽基;氘化苯基、氘化聯苯基、氘化三聯苯基、氘化萘基、氘化菲基、氘化蒽基、氘化苯並蒽基、氘化芴基、氘化基、氘化荧蒽基;未經取代的呋喃基、未經取代的吡咯基、未經取代的噻吩基、未經取代的咪唑基、未經取代的吡唑基、未經取代的***基、未經取代的四唑基、未經取代的噁唑基、未經取代的異噁唑基、未經取代的噻唑基、未經取代的異噻唑基、未經取代的噁二唑基、未經取代的噻二唑基、未經取代的吡啶基、未經取代的噠嗪基、未經取代的嘧啶基、未經取代的吡嗪基、未經取代的三嗪基、未經取代的吲哚基、未經取代的異吲哚基、未經取代的苯並呋喃基、未經取代的異苯並呋喃基、未經取代的苯並噻吩基、未經取代的異苯並噻吩基、未經取代的吲哚嗪基、未經取代的喹嗪基、未經取代的喹啉基、未經取代的異喹啉基、未經取代的噌啉基、未經取代的酞嗪基、未經取代的喹唑啉基、未經取代的喹喔啉基、未經取代的苯並咪唑、未經取代的苯並噁唑基、未經取代的苯並噻唑基、未經取代的吲唑基、未經取代的苯並異噁唑基、未經取代的苯並異噻唑基、、未經取代的二苯並呋喃基、未經取代的二苯並噻吩基、未經取代的咔唑基、未經取代的二咔唑基、未經取代的香豆素基、未經取代的色烯基、未經取代的菲基、未經取代的吖啶基、未經取代的啡啉基、未經取代的吩嗪基、未經取代的吩噻嗪基、未經取代的吩噁嗪基、未經取代的氮雜三亞苯基、二氮雜三亞苯基、未經取代的呫噸基、未經取代的氮雜咔唑基、未經取代的氮雜苯並呋喃基、未經取代的氮雜苯並噻吩基、未經取代的苯並呋喃苯並噻吩基、未經取代的苯並噻吩苯並噻吩基、未經取代的二苯並呋喃萘基、未經取代的二苯並噻吩萘基、未經取代的二萘噻吩噻吩苯基、未經取代的二萘噻吩噻吩苯基、未經取代的二萘咔唑基、未經取代的二苯並氮雜基、未經取代的三苯並氮雜基、未經取代的二苯並氧雜基、未經取代的三苯並氧雜基;具有至少一官能基的苯基、具有至少一官能基的聯苯基、具有至少一官能基的三聯苯基、具有至少一官能基的萘基、具有至少一官能基的菲基、具有至少一官能基的蒽基、具有至少一官能基的苯並蒽基、未具有至少一官能基的芴基、具有至少一官能基的基和具有至少一官能基的荧蒽基;其中,該至少一官能基是選自於由下列所構成的群組:氰基、硝基、三氟甲基、氟基和氯基。
- 如請求項1所述之化合物,其中L1和L2各自獨立選自於由下列所構成的群組:
- 如請求項1所述之化合物,其中該化合物是選自於由下列所構成的群組:化合物13; 化合物14; 化合物15;化合物28; 化合物29; 化合物30;
- 一種有機電子裝置,其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層,其中該有機層包括如請求項1至9中任一項所述的化合物。
- 如請求項10所述的有機電子裝置,其中該有機電子裝置為一有機發光二極體。
- 如請求項11所述的有機電子裝置,其中該有機發光二極體包括:一電洞注入層,其形成於該第一電極上;一電洞傳輸層,其形成於該電洞注入層上;一發光層,其形成於該電洞傳輸層上;一電子傳輸層,其形成於該發光層上,該有機層為該電子傳輸層;和一電子注入層,其形成於該電子傳輸層和該第二電極之間。
- 如請求項11所述的有機電子裝置,其中該有機發光二極體包括:一電洞注入層,其形成於該第一電極上;一電洞傳輸層,其形成於該電洞注入層上;一發光層,其形成於該電洞傳輸層上;一電洞阻擋層,其形成於該發光層上,該有機層為該電洞阻擋層;一電子傳輸層,其形成於該電洞阻擋層上;和一電子注入層,其形成於該電子傳輸層和該第二電極之間。
- 如請求項10所述的有機電子裝置,其中該化合物是選自於由下列所構成的群組:
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