JP4904002B2 - スピロシクロペンタフェナントレンフルオレン系化合物及びそれを利用した有機el素子 - Google Patents
スピロシクロペンタフェナントレンフルオレン系化合物及びそれを利用した有機el素子 Download PDFInfo
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- JP4904002B2 JP4904002B2 JP2005005273A JP2005005273A JP4904002B2 JP 4904002 B2 JP4904002 B2 JP 4904002B2 JP 2005005273 A JP2005005273 A JP 2005005273A JP 2005005273 A JP2005005273 A JP 2005005273A JP 4904002 B2 JP4904002 B2 JP 4904002B2
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- 150000001875 compounds Chemical class 0.000 title claims description 46
- 239000010410 layer Substances 0.000 claims description 45
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- 125000000217 alkyl group Chemical group 0.000 claims description 11
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
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- HJDKCHUESYFUMG-UHFFFAOYSA-N cycloocta-1,5-diene;nickel Chemical compound [Ni].C1CC=CCCC=C1 HJDKCHUESYFUMG-UHFFFAOYSA-N 0.000 description 2
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- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
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- SQTPFYJEKHTINP-UHFFFAOYSA-N 2-bromophenanthrene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3C=CC2=C1 SQTPFYJEKHTINP-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
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- 125000003282 alkyl amino group Chemical group 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 238000005401 electroluminescence Methods 0.000 description 1
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- 239000012776 electronic material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229920000327 poly(triphenylamine) polymer Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09B—EDUCATIONAL OR DEMONSTRATION APPLIANCES; APPLIANCES FOR TEACHING, OR COMMUNICATING WITH, THE BLIND, DEAF OR MUTE; MODELS; PLANETARIA; GLOBES; MAPS; DIAGRAMS
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- C08G73/0611—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polypyrroles
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
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- G—PHYSICS
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- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/018—Input/output arrangements for oriental characters
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- G06Q—INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR ADMINISTRATIVE, COMMERCIAL, FINANCIAL, MANAGERIAL OR SUPERVISORY PURPOSES; SYSTEMS OR METHODS SPECIALLY ADAPTED FOR ADMINISTRATIVE, COMMERCIAL, FINANCIAL, MANAGERIAL OR SUPERVISORY PURPOSES, NOT OTHERWISE PROVIDED FOR
- G06Q50/00—Information and communication technology [ICT] specially adapted for implementation of business processes of specific business sectors, e.g. utilities or tourism
- G06Q50/10—Services
- G06Q50/20—Education
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- H—ELECTRICITY
- 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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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1441—Heterocyclic
- C09K2211/1475—Heterocyclic containing nitrogen and oxygen as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1483—Heterocyclic containing nitrogen and sulfur as heteroatoms
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Description
2,7−ジブロモフルオレン(18.9g、58.32mmol)をt−ブチルヒドロパーオキシド(70wt% in water)(97mL)に溶かし、CrO3(0.3g)を添加した後、常温で12時間撹拌した。
[合成例2:4−(4H−シクロペンタ[def]フェナントレニル)−2,7−ジブロモ−4−スピロフルオレンの製造]
2−ブロモフェナントレン(Synthetic communication,9(5),377(1979)参照;20g、77.8mmol)を無水THF(300mL)に溶かした後、反応条件を−78℃に冷却させた。前記混合物に2.5Mノルマルブチルリチウム(62.4mL、156mmol)を添加し、30分間の冷却下で撹拌した。2,7−ジブロモフルオレン−4−オン(24.67g、73mmol)を無水THF(500mL)に溶かしてゆっくり滴加した後、30分間冷却しつつ撹拌した。
MASS(m/z):500(M+2)、419、339、263、207、169
[合成例3:ポリ(スピロシクロペンタフェナントレンフルオレン)の合成]
シュレンクフラスコ内部の水分を真空及び窒素置換で完全に除去した後、ビス1,5−シクロオクタジエンニッケル(O)0.444g(1.614mmol)と、2,2’−ビピリジン0.252g(1.614mmol)とをグローブボックス内に投入した後、フラスコ内部を真空及び窒素に置換した。
基板上部にITO(Indium−Tin Oxide)をコーティングしてITO層を有する透明電極基板を得た。前記ITO層を感光性樹脂とエッチャントとを利用して所望の形にパターニングし、UVを利用して洗浄した。その上に、伝導性バッファ層としてBayer社のBatron P 4083を約80nmの厚さにコーティングした後、180℃で約1時間ベーキングした。次に、合成例4によって製造された高分子をトルエンに溶解させて製造された高分子溶液を、前記バッファ層上にスピンコーティングし、ベーキング処理後に真空オーブン内から溶媒を完全に除去して発光層を形成させた。この時、前記高分子溶液は、スピンコーティングに適用する以前に0.2mmフィルタで濾過され、高分子薄膜の厚さは、前記高分子溶液の濃度とスピン速度とを調節することによって、約80nmになるように調節された。次に、前記発光層上部に真空蒸着器を利用し、真空度を4×10−6torr以下に保持しつつ、CaとAlとを順次に蒸着した。蒸着時の膜厚及び膜の成長速度は、クリスタルセンサを利用して調節した。このように製作された電界発光素子は、ITO/ポリチオフェン誘導体(PEDOT)/発光高分子/Ca/Alの構造を有し、発光面積は4mm2であった。
Claims (11)
- 下記化学式1で表されるスピロシクロペンタフェナントレンフルオレン系化合物:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12は、互いに独立して、水素原子、ハロゲン原子、ヒドロキシ基、置換されたまたは非置換のアミノ基、シアノ基、置換されたまたは非置換の炭素数1〜20のアルキル基、置換されたまたは非置換の炭素数3〜20のシクロアルキル基、置換されたまたは非置換の炭素数1〜20のアルコキシ基、置換されたまたは非置換の炭素数6〜30のアリール基、置換されたまたは非置換の炭素数6〜30のアリールアルキル基、置換されたまたは非置換の炭素数2〜30のヘテロアリール基からなる群から選択され、
R1、R2、R3、R4、R5、R6、R7、R8のうち2組以上の隣接した置換基、ならびに、R9及びR10、R11及びR12の少なくとも一方が互いに連結されて飽和または不飽和環を形成していてもよく、
mは2ないし5,000の実数である。 - アリーレン(Ar)繰り返し単位をさらに含み、下記化学式2で表される、請求項1に記載のスピロシクロペンタフェナントレンフルオレン系化合物:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12は前述の通りであり、
mは2ないし5,000の実数であり、
nは0.01〜1.0の実数である。 - 前記Arは、下記化学式3で表される群から選択されたいずれかの構造を有する、請求項2に記載のスピロシクロペンタフェナントレンフルオレン系化合物:
R13、R14、R15及びR16は、互いに独立して、水素原子、ヒドロキシ基、置換されたまたは非置換のアミノ基、シアノ基、ハロゲン原子、置換されたまたは非置換の炭素数1〜20のアルキル基、置換されたまたは非置換の炭素数3〜20のシクロアルキル基、置換されたまたは非置換の炭素数1〜20のアルコキシ基、置換されたまたは非置換の炭素数6〜30のアリール基、および、置換されたまたは非置換の炭素数2〜30のヘテロアリール基からなる群より選択される。 - 前記化合物は、下記化学式4で表されることを特徴とする請求項1に記載のスピロシクロペンタフェナントレンフルオレン系化合物:
式中、mは2ないし5,000の実数である。 - 前記化合物は、下記化学式5で表される化合物であることを特徴とする請求項2に記載のスピロシクロペンタフェナントレンフルオレン系化合物:
- 前記化合物は、下記化学式6で表される化合物であることを特徴とする請求項5に記載のスピロシクロペンタフェナントレンフルオレン系化合物:
- 1対の電極間に有機膜を含む有機EL素子において、
前記有機膜は、請求項1ないし6のうちいずれか1項に記載のスピロシクロペンタフェナントレンフルオレン系化合物を含むことを特徴とする有機EL素子。 - 前記有機膜は、発光層、ホール輸送層または電子輸送層であることを特徴とする請求項7に記載の有機EL素子。
- 前記有機膜は、ドーパントをさらに含む発光層であることを特徴とする請求項7または8に記載の有機EL素子。
- 前記発光層における前記スピロシクロペンタフェナントレンフルオレン系化合物の含有量は、発光層の形成材料の総重量100質量部を基準として、30ないし80質量部であることを特徴とする請求項9に記載の有機EL素子。
- 前記スピロシクロペンタフェナントレンフルオレン系化合物の数平均分子量は、10,000以上であることを特徴とする請求項7〜10のいずれか1項に記載の有機EL素子。
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