JP4642016B2 - 有機電界発光素子及び白金化合物 - Google Patents
有機電界発光素子及び白金化合物 Download PDFInfo
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- JP4642016B2 JP4642016B2 JP2006507730A JP2006507730A JP4642016B2 JP 4642016 B2 JP4642016 B2 JP 4642016B2 JP 2006507730 A JP2006507730 A JP 2006507730A JP 2006507730 A JP2006507730 A JP 2006507730A JP 4642016 B2 JP4642016 B2 JP 4642016B2
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- 150000003058 platinum compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
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- PCPQWYHRMVULIX-UHFFFAOYSA-P [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;dinitrate Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 PCPQWYHRMVULIX-UHFFFAOYSA-P 0.000 claims description 10
- BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 8
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
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- 0 CC(c1cccc(C(c(c(N)c2)c3c(C4(*)N)c2N)(N)N)*1*3(c1c2c(N)c3)*5c4cccc5C2(N)N)(c1c3N)N Chemical compound CC(c1cccc(C(c(c(N)c2)c3c(C4(*)N)c2N)(N)N)*1*3(c1c2c(N)c3)*5c4cccc5C2(N)N)(c1c3N)N 0.000 description 5
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- 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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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/311—Phthalocyanine
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Description
(1)一対の電極間に発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、下記一般式(4)で表される化合物の少なくとも1種を有機層に含有することを特徴とする有機電界発光素子。
(2)一般式(4)において、M 41 が銅イオン又は白金イオンであることを特徴とする(1)項に記載の有機電界発光素子。
(4)一般式(6)で表される化合物。
(5)一般式(4)で表される化合物がりん光を発する事を特徴とする(1)〜(3)項のいずれか1項に記載の有機電界発光素子。
(6)発光層中に少なくとも1種のホスト材料、及び、一般式(4)で表される化合物を少なくとも1種含むことを特徴とする(1)〜(3)及び(5)項のいずれか1項に記載の有機電界発光素子。
(7)発光層中のホスト材料が錯体である事を特徴とする(6)項に記載の有機電
界発光素子。
(8)発光層中にホスト材料を2種以上含むことを特徴とする(6)又は(7)項に記載の有機電界発光素子。
本発明の上記及び他の特徴及び利点は、添付の図面とともに考慮することにより、下記の記載からより明らかになるであろう。
まず、一般式(1)で表される化合物について説明する。
Q11は、Q11が結合する炭素原子2つとこれらの炭素原子に直接結合している窒素原子とを含んで、含窒素へテロ環を形成する原子群を表す。Q11で形成される含窒素へテロ環の環員数としては特に限定されないが、環員数12〜20が好ましく、環員数14〜16がより好ましく、環員数16がさらに好ましい。
また、一般式(1)で表される化合物としては、一般式(11)または一般式(15)で表される化合物も好ましい。一般式(11)で表される化合物は、一般式(12)で表される化合物またはその互変異性体、一般式(13)で表される化合物またはその互変異性体、一般式(14)で表される化合物またはその互変異性体が好ましく、一般式(12)で表される化合物またはその互変異性体、一般式(13)で表される化合物またはその互変異性体がより好ましく、一般式(12)で表される化合物またはその互変異性体がさらに好ましい。
Z21、Z22、Z23、Z24、Z25、Z26、M21はそれぞれ前記Z11、Z12、Z13、Z11、Z12、Z13、M11と同義であり、好ましい範囲も同じである。
Q31、Q32、Z31、Z32、Z33、Z34、Z35、Z36、X31、X32、X33、X34はそれぞれ前記一般式(2)のQ21、Q22、Z21、Z22、Z23、Z24、Z25、Z26、X21、X22、X23、X24と同義であり、好ましい範囲も同じである。
Z41、Z42、Z43、Z44、Z45、Z46、X41、X42、X43、X44、M41は前記一般式(2)のZ21、Z22、Z23、Z24、Z25、Z26、X21、X22、X23、X24、M21と同義であり、好ましい範囲も同じである。
R51、R52、R53、R54、R55、R56、Z51、Z52、Z53、Z54、Z55、Z56、X51、X52、X53、X54はそれぞれ前記一般式(3)及び(4)のR31、R32、R43、R44、R45、R46、Z41、Z42、Z43、Z44、Z45、Z46、X41、X42、X43、X44と同義であり、好ましい範囲も同じである。
R63、R64、R65、R66、Z61、Z62、Z63、Z64、Z65、Z66、X61、X62、X63、X64はそれぞれ前記一般式(4)のR43、R44、R45、R46、Z41、Z42、Z43、Z44、Z45、Z46、X41、X42、X43、X44と同義であり、好ましい範囲も同じである。
Z101、Z102、Z103はそれぞれ置換もしくは無置換の炭素原子又は窒素原子を表す。Z101、Z102、Z103の少なくとも一つが窒素原子であることが好ましい。
Z501、Z502、Z503、L501、L502、L503、L504、Q501、Q502、Q503、M501はそれぞれ前記Z101、Z102、Z103、L101、L102、L103、L104、Q101、Q103、Q102、M101と同義であり、好ましい範囲も同じである。
Z201、Z202、Z203、Z207、Z208、Z209、L201、L202、L203、L204、M201はそれぞれ前記Z101、Z102、Z103、Z101、Z102、Z103、L101、L102、L103、L104、M101と同義であり、好ましい範囲も同じである。Z204、Z205、Z206、Z210、Z211、Z212はそれぞれ置換または無置換の炭素原子又は窒素原子を表し、置換または無置換の炭素原子が好ましい。
L201〜L204の組み合わせは、L201、L202、L203、L204がそれぞれアルキレン基であることが好ましく、L201とL203がそれぞれ単結合であり、L202とL204がそれぞれアルキレン基であることがより好ましい。Z204、Z206、Z210、Z212の組み合わせは、Z204、Z206、Z210、Z212の少なくとも一つがフッ素置換炭素原子であることが好ましく、Z204、Z206、Z210、Z212がそれぞれフッ素置換炭素原子であることがより好ましい。Z202、Z208は、それぞれ独立にアルキル基、アルコキシ基、またはジアルキルアミノ基のいずれかで置換された炭素原子であることが好ましい。
Z301、Z302、Z303、Z304、Z305、Z306、Z307、Z308、Z309、Z310、L301、L302、L303、L304、M301はそれぞれ前記Z201、Z202、Z203、Z204、Z206、Z207、Z208、Z209、Z210、Z212、L101、L102、L103、L104、M101と同義であり、好ましい範囲も同じである。
L301〜L304の組み合わせは、L301、L302、L303、L304がそれぞれアルキレン基であることが好ましく、L301とL303がそれぞれ単結合であり、L302とL304がそれぞれアルキレン基であることがより好ましい。Z304、Z305、Z309、Z310の組み合わせは、Z304、Z305、Z309、Z310の少なくとも二つがそれぞれ窒素原子であることが好ましい。Z302、Z307は、それぞれ独立にアルキル基、アルコキシ基、またはジアルキルアミノ基のいずれかで置換された炭素原子であることが好ましい。
Z401、Z402、Z403、Z404、Z405、Z406、Z407、Z408、Z409、Z410、Z411、Z412、L401、L402、L403、L404、M401はそれぞれ前記Z201、Z202、Z203、Z204、Z205、Z206、Z207、Z208、Z209、Z210、Z211、Z212、L101、L102、L103、L104、M101と同義であり、好ましい範囲も同じである。
L401〜L404の組み合わせは、L401、L402、L403、L404がそれぞれアルキレン基であることが好ましく、L401とL403がそれぞれ単結合であり、L402とL404がそれぞれアルキレン基であることがより好ましい。Z404、Z406、Z410、Z412の組み合わせは、Z404、Z406、Z410、Z412の少なくとも一つがフッ素置換炭素原子であることが好ましく、Z404、Z406、Z410、Z412がそれぞれフッ素置換炭素原子であることがより好ましい。Z402、Z408は、それぞれ独立にアルキル基、アルコキシ基、またはジアルキルアミノ基のいずれかで置換された炭素原子であることが好ましい。
Z601、Z602、Z603、Z604、Z605、Z606、Z607、Z608、Z609、Z610、Z611、Z612、L601、L602、L603、L604、M601はそれぞれ前記Z201、Z202、Z203、Z207、Z208、Z209、Z204、Z205、Z206、Z210、Z211、Z212、L101、L102、L103、L104、M101と同義であり、好ましい範囲も同じである。
L601〜L604の組み合わせは、L601、L602、L603、L604がそれぞれアルキレン基であることが好ましく、L601とL603がそれぞれ単結合であり、L602とL604がそれぞれアルキレン基であることがより好ましい。Z607、Z609、Z610、Z612の組み合わせは、Z607、Z609、Z610、Z612の少なくとも一つがフッ素置換炭素原子であることが好ましく、Z607、Z609、Z610、Z612がそれぞれフッ素置換炭素原子であることがより好ましい。Z602、Z605は、それぞれ独立にアルキル基、アルコキシ基、またはジアルキルアミノ基のいずれかで置換された炭素原子であることが好ましい。
Z701、Z702、Z703、Z704、Z705、Z706、Z707、Z708、Z709、Z710、L701、L702、L703、L704、M701はそれぞれ前記Z201、Z202、Z203、Z207、Z208、Z209、Z204、Z206、Z210、Z212、L101、L102、L103、L104、M101と同義であり、好ましい範囲も同じである。
L701〜L704の組み合わせは、L701、L702、L703、L704がそれぞれアルキレン基であることが好ましく、L701とL703がそれぞれ単結合であり、L702とL704がそれぞれアルキレン基であることがより好ましい。Z707、Z708、Z709、Z710の組み合わせは、Z707、Z708、Z709、Z710の少なくとも二つがそれぞれ窒素原子であることが好ましい。Z702、Z705は、それぞれ独立にアルキル基、アルコキシ基、またはジアルキルアミノ基のいずれかで置換された炭素原子であることが好ましい。
Z801、Z802、Z803、Z804、Z805、Z806、Z807、Z808、Z809、Z810、Z811、Z812、L801、L802、L803、L804、M801、X801、X802はそれぞれ前記Z201、Z202、Z203、Z207、Z208、Z209、Z204、Z205、Z206、Z210、Z211、Z212、L101、L102、L103、L104、M101、X401、X402と同義であり、好ましい範囲も同じである。
L801〜L804の組み合わせは、L801、L802、L803、L804がそれぞれアルキレン基であることが好ましく、L801とL803がそれぞれ単結合であり、L802とL804がそれぞれアルキレン基であることがより好ましい。Z807、Z809、Z810、Z812の組み合わせは、Z807、Z809、Z810、Z812の少なくとも一つがフッ素置換炭素原子であることが好ましく、Z807、Z809、Z810、Z812がそれぞれフッ素置換炭素原子であることがより好ましい。Z802、Z805は、それぞれ独立にアルキル基、アルコキシ基、またはジアルキルアミノ基のいずれかで置換された炭素原子であることが好ましい。
本発明の発光素子は、本発明の化合物を利用する素子である点以外は通常の発光システム、駆動方法、利用形態などを用いることができる。一般式(1)等で表される化合物を発光材料または正孔注入材料・正孔輸送材料として利用する物が好ましい。発光材料として用いる場合は、紫外発光であっても赤外発光であっても良く、また蛍光発光であってもりん光発光であっても良い。代表的な発光素子として有機EL(エレクトロルミネッセンス)素子を挙げることができる。
陽極の作製には材料によって種々の方法が用いられるが、例えばITOの場合、電子ビーム法、スパッタリング法、抵抗加熱蒸着法、化学反応法(ゾルーゲル法など)、酸化インジウムスズの分散物の塗布などの方法で膜形成される。
陽極は洗浄その他の処理により、素子の駆動電圧を下げたり、発光効率を高めることも可能である。例えばITOの場合、UV−オゾン処理、プラズマ処理などが効果的である。
陰極の作製には電子ビーム法、スパッタリング法、抵抗加熱蒸着法、コーティング法、転写法などの方法が用いられ、金属を単体で蒸着することも、二成分以上を同時に蒸着することもできる。さらに、複数の金属を同時に蒸着して合金電極を形成することも可能であり、またあらかじめ調整した合金を蒸着させてもよい。
陽極及び陰極のシート抵抗は低い方が好ましく、数百Ω/□以下が好ましい。
発光層の形成方法は、特に限定されるものではないが、抵抗加熱蒸着、電子ビーム、スパッタリング、分子積層法、コーティング法、インクジェット法、印刷法、LB法、転写法などの方法が用いられ、好ましくは抵抗加熱蒸着、コーティング法である。
電子注入層、電子輸送層の形成方法としては、真空蒸着法やLB法、前記電子注入輸送材料を溶媒に溶解または分散させてコーティングする方法、インクジェット法、印刷法、転写法などが用いられる。コーティング法の場合、樹脂成分と共に溶解または分散することができ、樹脂成分としては例えば、正孔注入輸送層の場合に例示したものが適用できる。
保護層の形成方法についても特に限定はなく、例えば真空蒸着法、スパッタリング法、反応性スパッタリング法、MBE(分子線エピタキシ)法、クラスターイオンビーム法、イオンプレーティング法、プラズマ重合法(高周波励起イオンプレーティング法)、プラズマCVD法、レーザーCVD法、熱CVD法、ガスソースCVD法、コーティング法、印刷法、転写法を適用できる。
・化合物(1)の合成
Journal of Chemical Society, 5008,(1952)に記載の方法で合成した。1,3−ジイミノインドリン6g、2,6−ジアミノピリジン4.6gにn−ブタノール40mlを加え9時間加熱還流した。反応液を室温に戻し、ろ過後n−ブタノール40mlで洗浄した。これをニトロベンゼン50mlに分散させ、加熱還流させた後、冷却して再結晶することで化合物(1)を7g得た。
DP−EI−MS測定によりm/z=440のピークが検出された。
化合物(1)0.1g、PtCl2 0.21gにベンゾニトリル10mlを加え、窒素雰囲気下にて内温160℃で4時間撹拌した。反応液を室温に冷却し、ろ過しベンゾニトリル20ml、メタノール30mlで洗浄し化合物(8)を0.05g得た。
DP−EI−MS測定によりm/z=633のピークが検出された。
洗浄したITO基板を蒸着装置に入れ、CuPc(銅フタロシアニン)を10nm蒸着し、この上に、α−NPD(4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル)を厚さ40nmに蒸着し、この上に、Alq3(トリス(8−ヒドロキシキノリナト)アルミニウム錯体)を60nm蒸着した。有機薄膜上にパターニングしたマスク(発光面積が4mm×5mmとなるマスク)を設置し、蒸着装置内でフッ化リチウム3nmを蒸着し、この上に、アルミニウム400nmを蒸着した。東陽テクニカ製ソースメジャーユニット2400型(商品名)を用いて、直流定電圧をEL素子に印加し発光させ、その輝度をトプコン社の輝度計BM−8(商品名)を用いて測定した。その結果、200cd/m2で量子効率1.1%の緑色発光が得られた。また、100cd/m2で10時間発光させたところ、目視でダークスポットが確認された。
洗浄したITO基板を蒸着装置に入れ、本発明の化合物(8)を5nm蒸着し、この上に、α−NPD(4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル)を60nm蒸着し、この上に、Alq3(トリス(8−ヒドロキシキノリナト)アルミニウム錯体)を40nm蒸着した。有機薄膜上にパターニングしたマスク(発光面積が4mm×5mmとなるマスク)を設置し、蒸着装置内でフッ化リチウム3nmを蒸着し、この上に、アルミニウム400nmを蒸着した。東陽テクニカ製ソースメジャーユニット2400型を用いて、直流定電圧をEL素子に印加し発光させ、その輝度をトプコン社の輝度計BM−8を用いて測定した。その結果、200cd/m2で量子効率1.4%の緑色発光が得られた。また100cd/m2で10時間発光させたところ、目視でダークスポットは確認できなかった。
Claims (8)
- 一対の電極間に発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、下記一般式(4)で表される化合物の少なくとも1種を有機層に含有することを特徴とする有機電界発光素子。
- 一般式(4)において、M 41 が銅イオン又は白金イオンであることを特徴とする請求項1記載の有機電界発光素子。
- 前記有機層が発光層及び正孔注入層の少なくとも一層であることを特徴とする請求項1又は2に記載の有機電界発光素子。
- 一般式(4)で表わされる化合物がりん光を発する事を特徴とする請求項1〜3のいずれか1項に記載の有機電界発光素子。
- 発光層中に少なくとも1種のホスト材料、及び、一般式(4)で表される化合物を少なくとも1種含むことを特徴とする請求項1〜3及び5のいずれか1項に記載の有機電界発光素子。
- 発光層中のホスト材料が錯体である事を特徴とする請求項6に記載の有機電界発光素子。
- 発光層中にホスト材料を2種以上含むことを特徴とする請求項6又は7に記載の有機電界発光素子。
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