JP2014506003A - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP2014506003A JP2014506003A JP2013545076A JP2013545076A JP2014506003A JP 2014506003 A JP2014506003 A JP 2014506003A JP 2013545076 A JP2013545076 A JP 2013545076A JP 2013545076 A JP2013545076 A JP 2013545076A JP 2014506003 A JP2014506003 A JP 2014506003A
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- 238000005401 electroluminescence Methods 0.000 title claims description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 175
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 239000000203 mixture Substances 0.000 claims abstract description 107
- 239000000412 dendrimer Substances 0.000 claims abstract description 69
- 229920000736 dendritic polymer Polymers 0.000 claims abstract description 69
- 239000002904 solvent Substances 0.000 claims abstract description 37
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 24
- 238000009472 formulation Methods 0.000 claims abstract description 11
- 239000003446 ligand Substances 0.000 claims description 85
- 239000000463 material Substances 0.000 claims description 31
- 229940126062 Compound A Drugs 0.000 claims description 30
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 30
- 230000005525 hole transport Effects 0.000 claims description 20
- 239000006185 dispersion Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- -1 poly (p-phenylene) Polymers 0.000 description 94
- 239000010410 layer Substances 0.000 description 75
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 48
- 125000003118 aryl group Chemical group 0.000 description 44
- 229910052751 metal Inorganic materials 0.000 description 44
- 239000002184 metal Substances 0.000 description 44
- 125000000217 alkyl group Chemical group 0.000 description 37
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 230000032258 transport Effects 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000011159 matrix material Substances 0.000 description 25
- 238000000034 method Methods 0.000 description 25
- 238000002347 injection Methods 0.000 description 23
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
- 125000004429 atom Chemical group 0.000 description 19
- 230000000903 blocking effect Effects 0.000 description 19
- 239000000178 monomer Substances 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
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- 230000015572 biosynthetic process Effects 0.000 description 16
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- 230000008569 process Effects 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
- 150000004982 aromatic amines Chemical class 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 229920001400 block copolymer Polymers 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 10
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Natural products C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000021615 conjugation Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 229910052741 iridium Inorganic materials 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 125000006413 ring segment Chemical group 0.000 description 8
- 125000005259 triarylamine group Chemical group 0.000 description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 7
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- 239000000370 acceptor Substances 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 150000001454 anthracenes Chemical class 0.000 description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- 238000007641 inkjet printing Methods 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- 229950000688 phenothiazine Drugs 0.000 description 7
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000010948 rhodium Substances 0.000 description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 150000003457 sulfones Chemical class 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
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- 239000008346 aqueous phase Substances 0.000 description 6
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- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
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- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
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- 230000008878 coupling Effects 0.000 description 4
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- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
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- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- QYWFCUVQKBNIRJ-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)stibane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Sb](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QYWFCUVQKBNIRJ-UHFFFAOYSA-N 0.000 description 1
- YSPBORFVJLIOMX-UHFFFAOYSA-N tritert-butylarsane Chemical compound CC(C)(C)[As](C(C)(C)C)C(C)(C)C YSPBORFVJLIOMX-UHFFFAOYSA-N 0.000 description 1
- NZJQTVDLVPHKGY-UHFFFAOYSA-N tritert-butylstibane Chemical group CC(C)(C)[Sb](C(C)(C)C)C(C)(C)C NZJQTVDLVPHKGY-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- H05B33/00—Electroluminescent light sources
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- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
【選択図】 なし
Description
(1)基板、
(2)電極、高頻度で金属または無機であるが、有機または高分子伝導性材料から作られることもある、
(3)電極のムラの補正のための電荷注入層または中間層(「平坦化層」)、高頻度で伝導性ドープポリマーから作られる、
(4)有機半導体、
(5)場合によりさらなる電荷輸送または電荷注入または電荷ブロッキング層、
(6)対電極、(2)で言及された材料、
(7)封入。
(a)少なくとも1種のリン光性エミッター単位を含有する、または少なくとも1種のリン光性単位からなる化合物A、および
(b)少なくとも1種の放出単位を含有する、または放出単位からなる化合物B
を含み、2つの化合物AおよびBの少なくとも一方が、ポリマーまたはデンドリマーである、混合物の提供によって実現された。
1,3,5−トリアジン、たとえばスピロビフルオレントリアジン誘導体(たとえば、未公開出願DE102008064200.2に従って)
ピレン、アントラセン、テトラセン、フルオレン、スピロフルオレン、デンドリマー、テトラセン(たとえばルブレン誘導体)、1,10−フェナントロリン誘導体(JP2003−115387、JP2004−311184、JP−2001−267080、WO2002−043449)、シラシクロペンタジエン誘導体(EP1480280、EP1478032、EP1469533)、ボラン誘導体、たとえば、Siを加えたトリアリールボラン誘導体、
トリアゾール、たとえば
1,3,4−オキサジアゾール、たとえば
C1は、好ましくは、正孔輸送材料、電子輸送材料およびマトリックス材料、特に好ましくは上述した通りのマトリックス材料からなる単位から選択されるラジカルであり、前記正孔輸送材料および電子輸送材料は、上述および後述の通りである;
A1およびB1は、上記で定義した意味を有し、但し、上記で言及した放出単位/化合物は、水素原子を1位に担持せず、この位置でポリマー主鎖骨格と結合しており;
x、y、zは、それぞれの単位のモル百分率(mol−%)であり、ここで、x+y+z=1であり、ここで、x>0、y>0かつz≧0、好ましくはz>0である。
BBは、出現する毎に同一にまたは異なって、ポリマーの共役遮断を確保するポリマーの主鎖骨格単位を表し;故にBBは、好ましくは、上述した通りの共役遮断単位であり;
A1、B1、C1、x、yおよびzは、式(323)について定義したのと同じ意味を有し、但し、上記で言及した放出単位/化合物は水素原子を2位に担持せず、これらの位置でBBと結合している。
Aは、線状または分枝アルキレン、シクロアルキレン、アルキルシリレン、シリレン、アリールシリレン、アルキルアルコキシアルキレン、アリールアルコキシアルキレン、アルキルチオアルキレン、スルホン、アルキレンスルホン、スルホン酸化物、アルキレンスルホン酸化物からなる群から選択される共役遮断単位であり、ここで、各事例におけるアルキレン基は、互いに独立に、1〜12個のC原子を有し、ここで、1個以上のH原子は、F、Cl、Br、I、アルキル、ヘテロアルキル、シクロアルキル、アリールまたはヘテロアリールにより置きかえられていてもよく;
BBは、出現する毎に同一にまたは異なって、ポリマーの共役遮断を確保するポリマーの主鎖骨格単位を表し;
A1、B1およびC1は、式(323)について定義したのと同じ意味を有し、但し、B1の事例における上記で言及した放出単位/化合物は、水素原子を1位に担持せず、この位置でAと結合しており、A1の事例における上記で言及した放出単位/化合物は、水素原子を3位に担持せず、これらの位置でBBおよびAと結合しており;
x、zは、それぞれの単位のモル百分率(mol−%)であり、x+zは1であり、ここで、x>0かつz≧0、好ましくはz>0である。
BBは、ポリマーの共役遮断を確保するポリマーの主鎖骨格単位を表し;
A1、B1およびC1は、式(323)について定義したのと同じ意味を有し、但し、B1の事例における上記で言及した放出単位/化合物は、水素原子を1位に担持せず、この位置でBBと結合しており、A1の事例における上記で言及した放出単位/化合物は、水素原子を2位に担持せず、これらの位置でBBと結合しており;
x、zは、それぞれの単位のモル百分率(mol−%)であり、x+zは1であり、ここで、x>0かつz≧0、好ましくはz>0である。
nは、出現する毎に同一であるかまたは異なっており、好ましくは同一であり、好ましくは0、1、2または3に等しく;oおよびmは、3以上、好ましくは10以上、特に好ましくは20以上の単位の繰り返し数である。使用された他の添え字は、上記で定義したのと同じ意味を有する。
群1:ポリマーの正孔注入および/または正孔輸送特性を強化する単位;
群2:ポリマーの電子注入および/または電子輸送特性を強化する単位;
群3:群1および群2の個々の単位の組合せを有する単位;
群4:放出特徴を、電子リン光が電子蛍光の代わりに取得され得る程度に修正する単位;
群5:いわゆる一重項状態から三重項状態への移動を改善する単位;
群6:結果として生じるポリマーの放出色に影響を与える単位;
群7:典型的には骨格として使用される単位;
群8:結果として生じるポリマーの膜形態学的および/または流動学的特性に影響を与える単位。
ステップ1:
10mmolのビスアセチルアセトナートジクロロイリデートナトリウム(III)[770720−50−8]および24mmolのフェニルピリジンまたはフェニルイソキノリンの混合物を、50mlのガラス製アンプル中に真空(10-3mbar)で融解させる。アンプルを指示された温度で指示された時間加熱し、融解した混合物を磁気撹拌器の助力により撹拌する。冷却した後(注:アンプルは通常、加圧下である)、アンプルを開け、焼結ケーキを100gのガラスビーズ(直径3mm)とともに100mlのジクロロメタン中で3時間撹拌し、プロセス中に機械的に消化する。微細懸濁液をガラスビーズからデカントで除き、固体を吸引で濾過除去し、真空で乾燥させる。
このようにして取得された式[Ir(L)2Cl]2の粗製クロロ架橋ダイマーを、300mlのアセトンに懸濁し、4.4g(20mmol)のトリフルオロ酢酸銀(I)[2966−50−9]を懸濁液に添加し、混合物を2時間加熱還流する。冷却した後、塩化銀沈殿物を濾過除去し(P4)、4.8g(22mmol)の6−(4−ビニルフェニル)−2,4−ヘキサンジオン[59990−76−0]および10mlのトリエチルアミンを濾液に添加し、混合物を室温で20時間撹拌する。真空でのアセトンの除去後、残留物を200mlのジクロロメタンに溶かし、約10cmの長さを持つ酸化アルミニウムカラム(酸化アルミニウム、塩基性、活性グレード1)に通して濾過する。濾液の蒸発後、残留物を、酸化アルミニウム(酸化アルミニウム、塩基性、活性グレード(1)上で、ジクロロメタンを用いて、99.5%より高い、好ましくは99.9%より高い純度(HPLC)に到達するまでクロマトグラフィーにかける。
重合可能な基としてのスチリル基のための一般的な重合手順
表1において指示されている組成物中のモノマーM1〜M4およびスチレン(M5およびM6)を、20mlのトルエンに、1mol/lの濃度にて、保護ガス下、80℃で溶解する。64mgのAlBNをその後添加し、混合物を80℃でさらに2時間撹拌する。反応溶液を室温に冷却し、ポリマーは、100mlのメタノール中への沈殿(パスツールピペットをゆっくり使用する)によって取得される。白色沈殿物を吸引で濾過除去し、その後トルエンに再溶解し、メタノール中で再沈殿させ、吸引で濾過除去する。ポリマーを、真空乾燥キャビネット(VDC)内で乾燥させる。
重合可能な基としてのモノマーS1〜S9の鈴木重合のための一般的な重合手順
本発明によるポリマーP10〜P12およびP14〜P20ならびに比較用ポリマーP9およびP13は、WO03/048225A2に従い、下記のモノマー(百分率=mol%)を使用する鈴木カップリングによって合成する。
OLEDの生成
有機発光ダイオード(OLED)の生成については、文献において(たとえばWO2004/037887A2において)既に何度も記述されている。例として本発明を説明するために、表1〜3のポリマーP1〜P20を含むOLEDは、スピンコーティングによって生成される。
表6において指示されている組成物中のモノマーM1〜M4およびM7を、20mlのトルエンに、1mol/lの濃度にて、保護ガス下、室温で溶解する。5mol/%のsecブチルリチウム(ヘキサン中2M)をその後添加し、混合物を室温でさらに2時間撹拌する。表6において指示されている量のエチレンオキシドを、その後、末端基官能化のために反応溶液に添加する。重合は、カリウムtert−ブトキシドおよび用いられるトルエンに基づき0.5当量のDMSOの添加により、再開される。重合は、0.1Mメタノール性HCl溶液の添加により停止され、ポリマーは、100mlのメタノール中への沈殿(パスツールピペットをゆっくり使用する)によって取得される。白色沈殿物を吸引で濾過除去し、その後トルエンに再溶解し、メタノール中で再沈殿させ、吸引で濾過除去する。ポリマーをVDC内で乾燥させる。
PS−PEOブロックコポリマーおよび他の官能化合物を含む配合物
表8にまとめられている溶液は、次のようにして調製され、ここで、LiTrfは、トリフルオロメタンスルホン酸リチウム(LiTf、99.995%金属主成分;Aldrich)を表し、下記の式中のE3は、一重項青色エミッターである。E3は、WO2008/006449に従って合成される。
OLECの生成
層構造:ITO/PEDOT/中間層/EML/カソードを有するOLEC1〜4は、次のようにして構築される。中間層を除けば、生成は、例13において上述した通りのOLEDのものと同一である。
Claims (26)
- (c)少なくとも1種のリン光性エミッター単位を含有する化合物A、および
(d)少なくとも1種の放出単位を含有する化合物B
を含み、2つの化合物AおよびBの少なくとも一方が、ポリマーまたはデンドリマーである混合物。 - 前記ポリマーまたはデンドリマーは、ホスト材料の群から選択される少なくとも1種の繰り返し単位を含有する、請求項1に記載の混合物。
- 化合物Bの放出単位の少なくとも1種は蛍光エミッター単位である、請求項1又は2に記載の混合物。
- 化合物Bの放出単位の少なくとも1種はリン光性エミッター単位である、請求項1〜3の1項以上に記載の混合物。
- 前記リン光性エミッター単位は金属−リガンド配位化合物を含む単位である、請求項4に記載の混合物。
- 化合物AおよびBの一方がポリマーまたはデンドリマーであり、他方が4000g/mol以下の分子量を有する化合物である、請求項1〜5の1項以上に記載の混合物。
- 化合物Aおよび/または化合物Bが主鎖骨格を含有するポリマーである、請求項1〜5の1項以上に記載の混合物。
- 前記ポリマーは側鎖を有する、請求項7に記載の混合物。
- 前記ポリマーは共役または非共役ポリマーである、請求項7又は8に記載の混合物。
- 前記放出単位は、主鎖骨格中に繰り返し単位として存在するか、側鎖中に繰り返し単位として存在する、請求項9に記載の混合物。
- 電荷輸送単位が側鎖中に存在する、請求項8〜10の1項以上に記載の混合物。
- 電荷輸送単位が正孔輸送単位または電子輸送単位である、請求項11に記載の混合物。
- 電荷輸送単位が2つの側鎖中に存在し、一方の電荷輸送単位が正孔輸送単位であり、他方の電荷輸送単位が電子輸送単位である、請求項11又は12に記載の混合物。
- 主鎖骨格が、化合物Aのリン光性エミッター単位および化合物Bのエミッター単位の三重項準位よりも高いエネルギーを有する三重項準位を有する、請求項7〜13の1項以上に記載の混合物。
- 化合物A及びBが、各々、ポリマー又はデンドリマーである、請求項7〜14の1項以上に記載の混合物。
- 化合物A及びBの一方の放出バンドの最大値が、他方の化合物の放出バンドの最大値よりも短い波長である、請求項1〜15の1項以上に記載の混合物。
- 化合物Aの放出バンドが、化合物Bの吸収バンドの波長範囲と重複する波長範囲内である、請求項1〜16の1項以上に記載の混合物。
- 化合物Aの放出バンドの最大値は青色光の波長領域内であり、化合物Bの放出バンドの最大値は緑色または赤色光の波長領域内である、請求項1〜17の1項以上に記載の混合物。
- 化合物Aの放出バンドの最大値は緑色光の波長領域内であり、化合物Bの放出バンドの最大値は赤色光の波長領域内である、請求項1〜17の1項以上に記載の混合物。
- リン光性エミッター単位A1および放出単位B1を含有するポリマーまたはデンドリマーであって、前記単位A1とB1が互いに共役していないポリマーまたはデンドリマー。
- 単位A1は該ポリマーの主鎖骨格中の繰り返し単位であり、単位B1は該主鎖骨格に側鎖として連結している、請求項20に記載のポリマーまたはデンドリマー。
- 単位A1とB1は、該ポリマーの主鎖骨格中の繰り返し単位である、請求項20に記載のポリマーまたはデンドリマー。
- リン光性エミッター単位A1、また放出単位B1の双方が、金属−リガンド配位化合物単位である、請求項20〜22の1項以上に記載のポリマーまたはデンドリマー。
- 電子デバイスにおける請求項1〜19の1項以上に記載の混合物、あるいは、請求項20〜23の1項以上に記載のポリマーまたはデンドリマーの使用。
- 請求項1〜19の1項以上に記載の混合物、あるいは、請求項20〜23の1項以上に記載のポリマーまたはデンドリマーを含有する有機エレクトロルミネッセンス素子であって、好ましくは、有機発光素子(OLED)、有機発光電気化学電池(OLEC)、有機発光トランジスタ(OLET)、有機集積回路(O−lC)、有機電界効果トランジスタ(O−FET)、有機薄膜トランジスタ(O−TFT)、有機太陽電池(O−SC)、色素増感有機太陽電池(DSSC)、有機光学検波器、有機感光体、有機電場消光素子(O−FQD)、有機レーザーダイオード(O−レーザー)及び「有機プラズモン放出素子」からなる群から選択される有機エレクトロルミネッセンス素子。
- 請求項1〜19の1項以上に記載の混合物、または、請求項20〜23の1項以上に記載のポリマーもしくはデンドリマー、及び、少なくとも1種の溶剤を含有する配合物、特に、溶液、分散液又はエマルジョン。
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KR20220117199A (ko) | 2019-12-16 | 2022-08-23 | 미쯔비시 케미컬 주식회사 | 중합체, 유기 전계 발광 소자용 조성물, 정공 수송층 또는 정공 주입층 형성용 조성물, 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명 |
Also Published As
Publication number | Publication date |
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JP6538127B2 (ja) | 2019-07-03 |
WO2012084114A1 (de) | 2012-06-28 |
JP6258036B2 (ja) | 2018-01-10 |
DE112011104530A5 (de) | 2013-10-24 |
JP2017224836A (ja) | 2017-12-21 |
DE102010055901A1 (de) | 2012-06-28 |
US9478762B2 (en) | 2016-10-25 |
US20130277617A1 (en) | 2013-10-24 |
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