JP2002167365A - Bisphenylcyclohexane derivative - Google Patents
Bisphenylcyclohexane derivativeInfo
- Publication number
- JP2002167365A JP2002167365A JP2000364870A JP2000364870A JP2002167365A JP 2002167365 A JP2002167365 A JP 2002167365A JP 2000364870 A JP2000364870 A JP 2000364870A JP 2000364870 A JP2000364870 A JP 2000364870A JP 2002167365 A JP2002167365 A JP 2002167365A
- Authority
- JP
- Japan
- Prior art keywords
- group
- aromatic ring
- compound
- bisphenylcyclohexane
- ring group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 230000009477 glass transition Effects 0.000 abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 7
- 239000001257 hydrogen Substances 0.000 abstract description 7
- 238000000354 decomposition reaction Methods 0.000 abstract description 3
- 238000005401 electroluminescence Methods 0.000 abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- -1 Biphenylyl Chemical group 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000843 powder Substances 0.000 description 8
- 238000005019 vapor deposition process Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- NHPPIJMARIVBGU-UHFFFAOYSA-N 1-iodonaphthalene Chemical compound C1=CC=C2C(I)=CC=CC2=C1 NHPPIJMARIVBGU-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は蒸着プロセス耐熱性
に優れた化合物、およびその化合物を用いた電荷輸送材
料、有機電界発光素子に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound excellent in heat resistance of a vapor deposition process, a charge transport material using the compound, and an organic electroluminescent device.
【０００２】[0002]
【従来の技術】電子製品の材料化合物、特に有機電界発
光素子の電荷輸送材料として、分子中にトリフェニルア
ミンの４量体の構造を部分的に含む多様な構造の化合物
が提案されている（特開平7-126226号公報、特開平7-12
6615号公報）。2. Description of the Related Art As a material compound of an electronic product, in particular, as a charge transporting material of an organic electroluminescence device, a compound having a variety of structures including a tetramer structure of triphenylamine in a molecule has been proposed. JP-A-7-126226, JP-A-7-12
No. 6615).
【０００３】またこの中で、［２］式で表されるシクロ
ヘキサンの部分構造を有するトリフェニルアミンの４量
体が、有機電界発光素子の材料として提案されている
（特開平７−１２６２２６号公報の実施例３）。Among them, a tetramer of triphenylamine having a partial structure of cyclohexane represented by the formula [2] has been proposed as a material for an organic electroluminescent device (Japanese Patent Laid-Open No. 7-126226). Example 3).
【０００４】[0004]
【化２】 Embedded image
【０００５】この化合物はガラス転移点も高く、シクロ
ヘキサン環を含まない単純なトリフェニルアミンの４量
体化合物よりも高いイオン化ポテンシャル値を有してい
るため、多くの有機電界発光素子材料との組み合わせに
おいて高効率な有機電界発光素子を実現できることが期
待された。Since this compound has a high glass transition point and a higher ionization potential value than a simple triphenylamine tetramer compound containing no cyclohexane ring, it can be used in combination with many organic electroluminescent device materials. Therefore, it was expected that a highly efficient organic electroluminescent device could be realized.
【０００６】しかしながらこの化合物は、蒸着プロセス
における高温加熱条件下での安定性が低いため、蒸着プ
ロセス時に分解を起こし有機電界発光素子の特性に悪影
響を及ぼす可能性が高かった。そのため、この化合物を
使用して有機電界発光素子を作製する場合には比較的低
温での蒸着を余儀なくされるため、長い蒸着時間を要し
て生産効率が悪かった。However, since this compound has low stability under high-temperature heating conditions in the vapor deposition process, it is highly likely that it will be decomposed during the vapor deposition process and adversely affect the characteristics of the organic electroluminescent device. Therefore, when an organic electroluminescent device is manufactured using this compound, vapor deposition at a relatively low temperature is inevitable, and a long vapor deposition time is required, resulting in poor production efficiency.
【０００７】[0007]
【発明が解決しようとする課題】有機電界発光素子の製
造に際しては、蒸着温度を上げることによって蒸着時間
を短縮することが可能なので、蒸着プロセス時の耐熱性
が高いことが材料化合物に求められている。化合物が分
解する温度付近で蒸着プロセスを行うと、化学的に均一
な機能性膜が作製できず、有機電界発光素子の特性は大
きく低下する。In the production of an organic electroluminescent device, it is possible to shorten the vapor deposition time by increasing the vapor deposition temperature. Therefore, the material compound is required to have high heat resistance during the vapor deposition process. I have. If the vapor deposition process is performed near the temperature at which the compound decomposes, a chemically uniform functional film cannot be produced, and the characteristics of the organic electroluminescent device are greatly reduced.
【０００８】本発明は、［２］式の化合物の長所を損な
うことなく蒸着プロセス時の耐熱性を高めた化合物を電
荷輸送材料として提供すること、またその材料を使用し
た優れた特性を有する有機電界発光素子を提供すること
を目的としている。The present invention provides a compound having improved heat resistance during the vapor deposition process as a charge transporting material without impairing the advantages of the compound of the formula [2], and an organic material having excellent properties using the material. An object is to provide an electroluminescent device.
【０００９】[0009]
【課題を解決するための手段】本発明者らは前記した二
つの要件を同時に満足する化合物を探索した結果、一般
式［１］で表される化合物群が熱的に安定であることを
見出して本発明を完成するに至った。すなわち本発明
は、一般式［１］で表されるビスフェニルシクロヘキサ
ン誘導体である。Means for Solving the Problems The present inventors have searched for a compound that satisfies the above two requirements at the same time, and as a result, have found that a group of compounds represented by the general formula [1] is thermally stable. Thus, the present invention has been completed. That is, the present invention is a bisphenylcyclohexane derivative represented by the general formula [1].
【００１０】[0010]
【化３】 Embedded image
【００１１】（式中、Ａは置換基を有する炭素環式芳香
族環基、無置換の炭素多環式芳香族環基、置換もしくは
無置換の複素環式芳香族環基または置換もしくは無置換
の炭素環式脂肪族環基を表す。Ｒ１、Ｒ２、Ｒ３はそれ
ぞれに独立に、水素原子、ハロゲン原子、アルキル基、
アルコキシ基を表し、Ｒ４は水素原子、ハロゲン原子、
アルキル基、アルコキシ基、アミノ基、一置換アミノ基
または二置換アミノ基を表し、Ｒ５は水素原子、ハロゲ
ン原子、アルキル基、アルコキシ基、無置換のもしくは
二置換アミノ基で置換された炭素環式芳香族環基を表
し、Ｒ１とＲ５は縮合環を形成してもよい。）(Wherein A is a substituted carbocyclic aromatic ring group, an unsubstituted carbon polycyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group, or a substituted or unsubstituted Wherein R1, R2, and R3 each independently represent a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group, R4 represents a hydrogen atom, a halogen atom,
Represents an alkyl group, an alkoxy group, an amino group, a monosubstituted amino group or a disubstituted amino group, and R5 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a carbocyclic group substituted with an unsubstituted or disubstituted amino group. Represents an aromatic ring group, and R1 and R5 may form a condensed ring. )
【００１２】また、本発明は一般式［１］で表されるビ
スフェニルシクロヘキサン誘導体である耐熱性電荷輸送
材料用化合物である。Further, the present invention is a compound for a heat-resistant charge transporting material, which is a bisphenylcyclohexane derivative represented by the general formula [1].
【００１３】さらに本発明は一般式［１］で表されるビ
スフェニルシクロヘキサン誘導体を含む耐熱性電荷輸送
材料であり、またこの耐熱性電荷輸送材料を用いたこと
を特徴とする有機電界発光素子である。Further, the present invention relates to a heat-resistant charge transporting material containing a bisphenylcyclohexane derivative represented by the general formula [1], and an organic electroluminescent device characterized by using this heat-resistant charge transporting material. is there.
【００１４】本発明の一般式［１］で表されるビスフェ
ニルシクロヘキサン誘導体中、Ａで表される基としては
次のような基が挙げられる。置換基を有する炭素環式芳
香族環基の中で、置換基を有するフェニル基としては、
ビフェニリル基、トリフェニリル基、テトラフェニリル
基、トリチルフェニル基、メトキシフェニル基、トリル
基、キシリル基、メシチル基、エチルフェニル基、クメ
ニル基、トリフルオロメチルフェニル基、ジメチルアミ
ノフェニル基、ジフェニルアミノフェニル基、クロロフ
ェニル基、シアノフェニル基、ニトロフェニル基等があ
る。The group represented by A in the bisphenylcyclohexane derivative represented by the general formula [1] of the present invention includes the following groups. Among the substituted carbocyclic aromatic ring groups, as the substituted phenyl group,
Biphenylyl, triphenylyl, tetraphenylyl, tritylphenyl, methoxyphenyl, tolyl, xylyl, mesityl, ethylphenyl, cumenyl, trifluoromethylphenyl, dimethylaminophenyl, diphenylaminophenyl Chlorophenyl group, cyanophenyl group, nitrophenyl group and the like.
【００１５】無置換の炭素多環式芳香族環基としては、
インデニル基、インダニル基、ナフチル基、テトラリル
基、アズレニル基、ヘプタレニル基、アセナフチレニル
基、アセナフチル基、フェナレニル基、フルオレニル
基、アントリル基、アントラキノニル基、メチルアント
リル基、フェナントリル基、トリフェニレニル基、ピレ
ニル基、クリセニル基、ピセニル基、ペリレニル基、ペ
ンタフェニル基、ペンタセニル基、テトラフェニレニル
基、ヘキサフェニル基、ヘキサセニル基、ルビセニル
基、コロネニル基等がある。As the unsubstituted carbon polycyclic aromatic ring group,
Indenyl group, indanyl group, naphthyl group, tetralyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, acenaphthyl group, phenalenyl group, fluorenyl group, anthryl group, anthraquinonyl group, methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, Examples include a chrysenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, and a coronenyl group.
【００１６】次に複素環式芳香族環基としては、チオニ
ル基、フリル基、ピロリル基、イミダゾリル基、ベンゾ
フリル基、ピラゾリル基、オキサゾリル基、チアゾリル
基、イミダゾリル基、ピリジル基、ピラジニル基、ピリ
ミジニル基、ピリダジニル基、トリアジニル基、インド
リル基、キノリル基、イソキノリル基、フタラジニル
基、キノキサリニル基、キナゾリニル基、カルバゾリル
基、アクリジニル基、フェナジニル基、フルフリル基、
イソチアゾリル基、イソキサゾリル基、フラザニル基、
フェノキサジニル基、ベンゾチアゾリル基、ベンゾオキ
サゾリル基、ベンゾイミダゾリル基等がある。Next, as the heterocyclic aromatic ring group, a thionyl group, furyl group, pyrrolyl group, imidazolyl group, benzofuryl group, pyrazolyl group, oxazolyl group, thiazolyl group, imidazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group , Pyridazinyl group, triazinyl group, indolyl group, quinolyl group, isoquinolyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, acridinyl group, phenazinyl group, furfuryl group,
Isothiazolyl group, isoxazolyl group, furazanyl group,
Examples include a phenoxazinyl group, a benzothiazolyl group, a benzoxazolyl group, and a benzimidazolyl group.
【００１７】また炭素環式脂肪族環基としては、シクロ
ペンチル基、シクロヘキシル基、シクロヘプチル基、シ
クロオクチル基、ノルボレニル基、デカリル基、アダマ
ンチル基等がある。Examples of the carbocyclic aliphatic ring group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a norborenyl group, a decalyl group, an adamantyl group and the like.
【００１８】本発明のビスフェニルシクロヘキサン誘導
体の一般式［１］中、Ａで表される基として示した中で
も好ましいものは、電子供与性の置換基で置換された炭
素環式芳香族環基と、置換基を有する炭素多環式芳香族
環基または無置換の炭素多環式芳香族環基である。Of the bisphenylcyclohexane derivatives of the present invention, those represented by A in the general formula [1] are preferably a carbocyclic aromatic ring group substituted with an electron-donating substituent. And a substituted carbon polycyclic aromatic ring group or an unsubstituted carbon polycyclic aromatic ring group.
【００１９】発明者らは以下のような測定によって化合
物の熱的な安定性を評価した。まず液体クロマトグラフ
ィー分析にて純度１００％の化合物を金属容器に詰め、
電気炉内の窒素気流シリンダー中に置いて３０分間恒温
に保って熱分解させた。次にシリンダーを室温まで冷却
してから金属容器を取り出して、液体クロマトグラフィ
ーを用いて容器内の化合物の純度を測定した。この測定
を異なった温度で繰り返して化合物の１％が分解する温
度を求め、耐熱温度と称した。The inventors evaluated the thermal stability of the compound by the following measurements. First, 100% pure compound was packed in a metal container by liquid chromatography analysis.
The sample was placed in a nitrogen gas cylinder in an electric furnace and kept at a constant temperature for 30 minutes for pyrolysis. Next, after cooling the cylinder to room temperature, the metal container was taken out, and the purity of the compound in the container was measured using liquid chromatography. This measurement was repeated at different temperatures to determine the temperature at which 1% of the compound decomposed, and was referred to as the heat-resistant temperature.
【００２０】一般式［１］には含まれないが、一般式
［１］式で表されるシクロヘキサンの部分構造を有して
いるトリフェニルアミンの４量体であって、［２］式で
表される特開平７−１２６２２６号公報実施例３の化合
物の耐熱温度は２６７℃であった。Although not included in the general formula [1], it is a tetramer of triphenylamine having a partial structure of cyclohexane represented by the general formula [1], and is a tetramer of the formula [2] The heat resistance temperature of the compound of Example 3 in JP-A-7-126226 was 267 ° C.
【００２１】本発明者らはシクロヘキサンの部分構造を
有する種々の構造の化合物を合成して耐熱温度を比較し
た結果、一般式［１］で規定するように、Ａで表される
基を従来の無置換のフェニル基から置換基を有するフェ
ニル基、置換もしくは無置換の二環以上の炭素環式芳香
族環基、置換もしくは無置換の複素環式芳香族環基また
は置換もしくは無置換の炭素環式脂肪族環基に変えるこ
とによって、耐熱温度を向上させることができることを
見出した。As a result of synthesizing compounds having various structures having a partial structure of cyclohexane and comparing the heat-resistant temperatures, the present inventors have found that the group represented by A can be converted to a conventional group as defined by the general formula [1]. Unsubstituted phenyl to substituted phenyl, substituted or unsubstituted bicyclic or higher carbocyclic aromatic ring, substituted or unsubstituted heterocyclic aromatic ring, or substituted or unsubstituted carbocyclic It has been found that the heat resistance temperature can be improved by changing to a formula aliphatic ring group.
【００２２】化合物の耐熱温度が向上する理由は明らか
ではないが、Ａで表される基としては電子供与性の置換
基を有する炭素環式芳香族環基や、置換基を有する炭素
多環式芳香族環基または無置換の炭素多環式芳香族環基
であることが好ましい。Although the reason why the heat resistance temperature of the compound is improved is not clear, the group represented by A may be a carbocyclic aromatic ring group having an electron donating substituent or a carbon polycyclic group having a substituent. It is preferably an aromatic ring group or an unsubstituted carbon polycyclic aromatic ring group.
【００２３】例えば本発明の一般式［１］で表される誘
導体の具体的化合物である、Ａがp-tert-ブチルフェニ
ル基である［化４］式で表されるビスフェニルシクロヘ
キサン誘導体の耐熱温度は３７８℃であり、［２］式の
化合物より顕著に高かった。For example, the heat resistance of the bisphenylcyclohexane derivative represented by the formula [4], wherein A is a p-tert-butylphenyl group, which is a specific compound of the derivative represented by the general formula [1] of the present invention, The temperature was 378 ° C., which was significantly higher than the compound of the formula [2].
【００２４】[0024]
【化４】 Embedded image
【００２５】また、Ａがナフチル基である［化５］式で
表されるビスフェニルシクロヘキサン誘導体の耐熱温度
はさらに高く、３９１℃であった。The bisphenylcyclohexane derivative represented by the formula [5] wherein A is a naphthyl group had a higher heat-resistant temperature of 391 ° C.
【００２６】[0026]
【化５】 Embedded image
【００２７】しかも［化４］式の化合物は１５７℃、
［化５］式の化合物は１５９℃という高いガラス転移点
を有し、［２］式で表される特開平７−１２６２２６号
公報実施例３の化合物の１３９℃より顕著に高く、シク
ロヘキサン環構造を含まない［化６］式で表される一般
的なトリフェニルアミンの４量体化合物のガラス転移点
の１４２℃や、同じく５量体の１４５℃よりも勝ってい
た。Furthermore, the compound of the formula [4]
The compound of the formula [5] has a high glass transition point of 159 [deg.] C., is remarkably higher than the compound of the example 3 in JP-A-7-126226, 139 [deg.] C., and has a cyclohexane ring structure. Is higher than the glass transition point of 142 ° C. of the general triphenylamine tetramer compound represented by the formula [6] and 145 ° C. of the same pentamer.
【００２８】[0028]
【化６】 Embedded image
【００２９】本発明の化合物はウルマン反応をおこなう
ことで合成できる。さらに晶析や吸着、カラムクロマト
グラフィーを行うことによって精製でき、高純度品を得
ることができる。The compound of the present invention can be synthesized by carrying out an Ullmann reaction. Furthermore, purification can be performed by crystallization, adsorption, or column chromatography, and a highly purified product can be obtained.
【００３０】本発明の化合物の仕事関数は５．２〜５．
６ｅＶであり、電荷輸送材料として使用するのに十分な
特性を有している。The work function of the compound of the present invention is 5.2 to 5.
6 eV, which is sufficient for use as a charge transport material.
【００３１】本発明の一般式［１］で表されるビスフェ
ニルシクロヘキサン誘導体は、［２］式で表される特開
平７−１２６２２６号公報の化合物と比較して顕著に熱
的に安定である。その結果、蒸着プロセス時の高温に耐
えることができ、短時間で有機電界発光素子を容易に作
製することができる。また本発明の化合物は高いガラス
転移点を有するために、電荷輸送材料として形成された
機能膜は安定である。さらに有機電界発光素子や電子写
真用感光体に使用された場合は、高温環境下や発熱環境
下において優れた安定性を発揮することが可能になる。The bisphenylcyclohexane derivative of the present invention represented by the general formula [1] is remarkably more thermally stable than the compound of the formula [2] of JP-A-7-126226. . As a result, the organic electroluminescent device can withstand high temperatures during the vapor deposition process and can be easily manufactured in a short time. Further, since the compound of the present invention has a high glass transition point, the functional film formed as a charge transporting material is stable. Further, when used in an organic electroluminescent device or a photoconductor for electrophotography, excellent stability can be exhibited in a high-temperature environment or a heat-generating environment.
【００３２】[0032]
【発明の実施の形態】以下本発明の化合物の製造方法お
よび物性について、実施例により具体的に説明する。BEST MODE FOR CARRYING OUT THE INVENTION The production method and physical properties of the compound of the present invention will be specifically described below with reference to examples.
【００３３】[0033]
【実施例】〔実施例１〕４,４'-（９-シクロヘキシリデ
ン）ビス（Ｎ-（４'''-フェニルアミノ-４''-ビフェニ
リル）アニリン）７．５ｇ（１０mmol）、１-ヨード-４
-ｔｅｒｔ-ブチルベンゼン１３．０ｇ（５０mmol）、無
水炭酸カリウム８．３ｇ（６０mmol）、銅粉０．６４ｇ
（１０mmol）、トリデカン１００ｍｌを混合し、窒素雰
囲気下で還流して１０時間反応させた。反応生成物をト
ルエン２００ｍｌで抽出し、不溶分を濾別した。濾液を
濃縮乾固して粗製物を得て、シリカゲルを用いたカラム
クロマトグラフィーによって精製した。精製によって得
られた白色粉体は１．９ｇで、収率は１５％、融点は１
５０〜１８５℃であった。EXAMPLES Example 1 7.5 g (10 mmol) of 4,4 ′-(9-cyclohexylidene) bis (N- (4 ′ ″-phenylamino-4 ″ -biphenylyl) aniline) -Iodine-4
-tert-butylbenzene 13.0 g (50 mmol), anhydrous potassium carbonate 8.3 g (60 mmol), copper powder 0.64 g
(10 mmol) and 100 ml of tridecane, and the mixture was refluxed under a nitrogen atmosphere and reacted for 10 hours. The reaction product was extracted with 200 ml of toluene, and the insoluble matter was separated by filtration. The filtrate was concentrated to dryness to give a crude product, which was purified by column chromatography on silica gel. The white powder obtained by the purification was 1.9 g, the yield was 15%, and the melting point was 1
50-185 ° C.
【００３４】得られた白色粉体について、元素分析を実
施した。実測値は以下の通りであり、分子式がＣ94Ｈ96
Ｎ4となり、得られた白色粉体が［化４］式の構造であ
ると同定した。 理論値（炭素８８．１％）（水素７．５％）（窒素４．４％） 実測値（炭素８８．２％）（水素７．７％）（窒素４．１％）Elemental analysis was performed on the obtained white powder. The measured values are as follows, and the molecular formula is C94H96.
It became N4 and the obtained white powder was identified as having the structure of the formula [4]. Theoretical value (88.1% carbon) (7.5% hydrogen) (4.4% nitrogen) Actual value (88.2% carbon) (7.7% hydrogen) (4.1% nitrogen)
【００３５】〔実施例２〕４,４'-（９-シクロヘキシリ
デン）ビス（Ｎ-（４'''-フェニルアミノ-４''-ビフェ
ニリル）アニリン）７．５ｇ（１０mmol）、１-ヨード
ナフタレン１２．７ｇ（５０mmol）、無水炭酸カリウム
８．３ｇ（６０mmol）、銅粉０．６４ｇ（１０mmol）、
トリデカン１００ｍｌを混合し、窒素雰囲気下で還流し
て１０時間反応させた。反応生成物をトルエン２００ｍ
ｌで抽出し、不溶分を濾別した。濾液を濃縮乾固して粗
製物を得て、シリカゲルを用いたカラムクロマトグラフ
ィーによって精製した。精製によって得られた淡黄色粉
体は９．７ｇで、収率は７７％、融点は１８９〜２２１
℃であった。Example 2 7.5 g (10 mmol) of 4,4 ′-(9-cyclohexylidene) bis (N- (4 ′ ″-phenylamino-4 ″ -biphenylyl) aniline) 12.7 g (50 mmol) of iodonaphthalene, 8.3 g (60 mmol) of anhydrous potassium carbonate, 0.64 g (10 mmol) of copper powder,
100 ml of tridecane was mixed, and the mixture was refluxed under a nitrogen atmosphere and reacted for 10 hours. The reaction product is 200m of toluene
and the insolubles were filtered off. The filtrate was concentrated to dryness to give a crude product, which was purified by column chromatography on silica gel. The pale yellow powder obtained by the purification was 9.7 g, the yield was 77%, and the melting point was 189 to 221.
° C.
【００３６】得られた淡黄色粉体について、元素分析を
実施した。実測値は以下の通りであり、分子式がＣ94Ｈ
72Ｎ4となり、得られた淡黄色粉体が［化５］式の構造
であると同定した。 理論値（炭素８９．８％）（水素５．８％）（窒素４．５％） 実測値（炭素８９．５％）（水素５．４％）（窒素４．３％）The obtained pale yellow powder was subjected to elemental analysis. The measured values are as follows, and the molecular formula is C94H
72N4. The obtained pale yellow powder was identified to have the structure of the formula [5]. Theoretical value (89.8% carbon) (5.8% hydrogen) (4.5% nitrogen) Actual value (89.5% carbon) (5.4% hydrogen) (4.3% nitrogen)
【００３７】〔比較例１〕特開平７−１２６２２６号公
報の実施例３の化合物を、その実施例に記載された方法
で合成して、融点１６０〜１８３℃の淡黄色粉体として
［２］式の化合物を得た。[Comparative Example 1] The compound of Example 3 of JP-A-7-126226 was synthesized by the method described in the example to give [2] as a pale yellow powder having a melting point of 160 to 183 ° C. A compound of the formula is obtained.
【００３８】〔比較例２〕特開平７−１２６２２６号公
報の実施例１の化合物を、その実施例に記載された方法
で合成し、融点２４０〜２４４℃の淡黄色の粉体とし
て、［化６］式の化合物を得た。[Comparative Example 2] The compound of Example 1 of JP-A-7-126226 was synthesized by the method described in the example, and was converted into a pale yellow powder having a melting point of 240 to 244 ° C. 6] The compound of the formula was obtained.
【００３９】［実施例３］本発明と比較例の化合物につ
いて窒素気流シリンダ−と電気炉、液体クロマトグラフ
ィーを用いて、分解耐熱性を測定した。３０分間に化合
物の１％が分解する温度を耐熱温度とした。 ［化４］式の本発明実施例１の化合物 耐熱温度 ： ３７８℃ ［化５］式の本発明実施例２の化合物 耐熱温度 ： ３９１℃ ［２］式の比較例１の化合物 耐熱温度 ： ２６７℃[Example 3] The decomposition heat resistance of the compounds of the present invention and the comparative examples was measured using a nitrogen stream cylinder, an electric furnace and liquid chromatography. The temperature at which 1% of the compound decomposed in 30 minutes was defined as the heat resistant temperature. [Chemical formula 4] Compound of formula 1 of the present invention Heat-resistant temperature: 378 ° C [Chemical formula 5] Compound of formula 2 of the present invention Heat-resistant temperature: 391 ° C [2] Compound of formula 1 of comparative example Heat-resistant temperature: 267 ° C
【００４０】以上の結果から本発明の化合物が、比較例
の化合物と比べて、顕著に高い分解耐熱性を有すること
が明白である。From the above results, it is clear that the compound of the present invention has remarkably high decomposition heat resistance as compared with the compound of the comparative example.
【００４１】〔実施例４〕本発明と比較例の化合物につ
いて、ＤＳＣ（示差走査熱量計、マックサイエンス製）
によってガラス転移点を求めた。 ［化４］式の本発明実施例１の化合物 ガラス転移点 ： １５９℃ ［化５］式の本発明実施例２の化合物 ガラス転移点 ： １５７℃ ［２］式の比較例１の化合物 ガラス転移点 ： １３９℃ ［化６］式の比較例２の化合物 ガラス転移点 ： １４２℃[Example 4] DSC (differential scanning calorimeter, manufactured by Mac Science) for the compounds of the present invention and comparative examples
To determine the glass transition point. [Compound 4] Compound of formula 1 of the present invention glass transition point: 159 ° C. [Compound 5] Compound of formula 2 of the present invention Glass transition point: 157 ° C. [2] Compound of formula 1 of comparative example Glass transition Point: 139 ° C. Compound of Comparative Example 2 of Formula 6 Glass transition point: 142 ° C.
【００４２】以上の結果から本発明の化合物が、トリフ
ェニルアミン４量体群の中においても高いガラス転移点
を有することが明白である。From the above results, it is clear that the compound of the present invention has a high glass transition point even in the triphenylamine tetramer group.
【００４３】［実施例５］本発明と比較例の化合物につ
いて、表面分析計ＡＣ１（理研計器製）で仕事関数を測
定し、本発明の化合物を一般的な正孔輸送材料と比較し
た。測定結果を次に示す。 ［化４］式の本発明実施例１の化合物 仕事関数 ： ５．４ｅＶ ［２］式の比較例１の化合物 仕事関数 ： ５．４ｅＶExample 5 The work functions of the compounds of the present invention and the comparative examples were measured using a surface analyzer AC1 (manufactured by Riken Keiki), and the compounds of the present invention were compared with general hole transport materials. The measurement results are shown below. Compound of formula 1 of the present invention in Example 1 Work function: 5.4 eV Compound of formula [2] of Comparative example 1 Work function: 5.4 eV
【００４４】以上の結果から、本発明の化合物は従来の
正孔輸送材料と同じ仕事関数を有しており、正孔輸送材
料として適性であるといえる。From the above results, it can be said that the compound of the present invention has the same work function as a conventional hole transport material and is suitable as a hole transport material.
【００４５】[0045]
【発明の効果】本発明の化合物は耐熱温度が高いため熱
分解を起こしにくく、蒸着プロセスが行いやすいために
有機電界発光素子用の材料として適している。またガラ
ス転移点が高いので、作製した機能膜は電気的・化学的
に安定である。したがって、本発明の化合物を使用した
有機電界発光素子は、優れた環境安定性を発揮する。The compound of the present invention is suitable as a material for an organic electroluminescent device because it has a high heat-resistant temperature and does not easily cause thermal decomposition, and is easy to perform a vapor deposition process. Further, since the glass transition point is high, the produced functional film is electrically and chemically stable. Therefore, the organic electroluminescent device using the compound of the present invention exhibits excellent environmental stability.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 小松 志保子 茨城県つくば市御幸が丘45番地 保土谷化 学工業株式会社筑波研究所内 Ｆターム(参考） 3K007 AB06 AB11 AB14 DA01 DB03 EB00 4H006 AA01 AA03 AB90 ────────────────────────────────────────────────── ─── Continuing from the front page (72) Inventor Shihoko Komatsu 45 Miyukigaoka, Tsukuba, Ibaraki Prefecture F-term in Tsukuba Research Laboratory, Hodogaya Chemical Industry Co., Ltd. 3K007 AB06 AB11 AB14 DA01 DB03 EB00 4H006 AA01 AA03 AB90
Claims (7)
クロヘキサン誘導体。 【化１】 （式中、Ａは置換基を有する炭素環式芳香族環基、無置
換の炭素多環式芳香族環基、置換もしくは無置換の複素
環式芳香族環基または置換もしくは無置換の炭素環式脂
肪族環基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ独立し
て、水素原子、ハロゲン原子、アルキル基、アルコキシ
基を表し、Ｒ４は水素原子、ハロゲン原子、アルキル
基、アルコキシ基、アミノ基、一置換アミノ基または二
置換アミノ基を表し、Ｒ５は水素原子、ハロゲン原子、
アルキル基、アルコキシ基、無置換のもしくは二置換ア
ミノ基で置換された炭素環式芳香族環基を表し、Ｒ１と
Ｒ５は縮合環を形成してもよい。）1. A bisphenylcyclohexane derivative represented by the general formula [1]. Embedded image (Wherein A is a substituted carbocyclic aromatic ring group, an unsubstituted carbon polycyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group, or a substituted or unsubstituted carbon ring R 1, R 2, R 3 each independently represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group; R 4 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an amino group, Represents a monosubstituted amino group or a disubstituted amino group, and R5 represents a hydrogen atom, a halogen atom,
Represents an alkyl group, an alkoxy group, a carbocyclic aromatic ring group which is unsubstituted or substituted with a disubstituted amino group, and R1 and R5 may form a condensed ring. )
与性の置換基を有する炭素環式芳香族環基、置換基を有
する炭素多環式芳香族環基または無置換の炭素多環式芳
香族環基である請求項１記載のビスフェニルシクロヘキ
サン誘導体。2. In the general formula [1], A is a carbocyclic aromatic ring group having an electron donating substituent, a carbon polycyclic aromatic ring group having a substituent or an unsubstituted carbon atom. The bisphenylcyclohexane derivative according to claim 1, which is a polycyclic aromatic ring group.
ェニルシクロヘキサン誘導体である、請求項１記載の耐
熱性電荷輸送材料用化合物。3. The compound for a heat-resistant charge transporting material according to claim 1, which is a bisphenylcyclohexane derivative represented by the general formula [1].
［１］が置換基Ａとして電子供与性の置換基を有する炭
素環式芳香族環基、置換基を有する炭素多環式芳香族環
基または無置換の炭素多環式芳香族環基を有する、ビス
フェニルシクロヘキサン誘導体である請求項２〜請求項
３記載の耐熱性電荷輸送材料用化合物。4. A carbocyclic aromatic ring group having an electron donating substituent represented by the general formula [1], wherein the general formula [1] has a substituent A, and a carbon polycyclic ring having a substituent. The compound for a heat-resistant charge transporting material according to claim 2, which is a bisphenylcyclohexane derivative having an aromatic ring group or an unsubstituted carbon polycyclic aromatic ring group.
ェニルシクロヘキサン誘導体を含む耐熱性電荷輸送材
料。5. A heat-resistant charge transporting material containing the bisphenylcyclohexane derivative represented by the general formula [1].
与性の置換基を有する炭素環式芳香族環基、置換基を有
する炭素多環式芳香族環基または無置換の炭素多環式芳
香族環基である、ビスフェニルシクロヘキサン誘導体を
含む請求項５記載の耐熱性電荷輸送材料。6. In the general formula [1], A is a carbocyclic aromatic ring group having an electron-donating substituent, a carbon polycyclic aromatic ring group having a substituent, or an unsubstituted carbon atom. The heat-resistant charge transporting material according to claim 5, comprising a bisphenylcyclohexane derivative that is a polycyclic aromatic ring group.
を用いたことを特徴とする有機電界発光素子。7. An organic electroluminescent device comprising the heat-resistant charge transporting material according to claim 5.
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| JP2000364870A JP2002167365A (en) | 2000-11-30 | 2000-11-30 | Bisphenylcyclohexane derivative |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000364870A JP2002167365A (en) | 2000-11-30 | 2000-11-30 | Bisphenylcyclohexane derivative |
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| JP2002167365A true JP2002167365A (en) | 2002-06-11 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005063684A1 (en) * | 2003-12-26 | 2005-07-14 | Hodogaya Chemical Co., Ltd. | Tetramine compound and organic el device |
| JP2007531762A (en) * | 2004-03-31 | 2007-11-08 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Triarylamine compounds used as charge transport materials |
| US8716697B2 (en) | 2004-02-20 | 2014-05-06 | E I Du Pont De Nemours And Company | Electronic devices made with crosslinkable compounds and copolymers |
-
2000
- 2000-11-30 JP JP2000364870A patent/JP2002167365A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005063684A1 (en) * | 2003-12-26 | 2005-07-14 | Hodogaya Chemical Co., Ltd. | Tetramine compound and organic el device |
| JPWO2005063684A1 (en) * | 2003-12-26 | 2007-07-19 | 保土谷化学工業株式会社 | Tetramine compound and organic EL device |
| US7807274B2 (en) | 2003-12-26 | 2010-10-05 | Hodogaya Chemical Co., Ltd. | Tetramine compound and organic EL device |
| US7897816B2 (en) | 2003-12-26 | 2011-03-01 | Hodogaya Chemical Co., Ltd. | Tetramine compound and organic EL device |
| US7902402B2 (en) | 2003-12-26 | 2011-03-08 | Hodogaya Chemical Co., Ltd. | Tetramine compound and organic EL device |
| JP2011088928A (en) * | 2003-12-26 | 2011-05-06 | Hodogaya Chem Co Ltd | Tetramine compound and organic el element |
| JP4682042B2 (en) * | 2003-12-26 | 2011-05-11 | 保土谷化学工業株式会社 | Tetramine compound and organic EL device |
| US8716697B2 (en) | 2004-02-20 | 2014-05-06 | E I Du Pont De Nemours And Company | Electronic devices made with crosslinkable compounds and copolymers |
| JP2007531762A (en) * | 2004-03-31 | 2007-11-08 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Triarylamine compounds used as charge transport materials |
| US8236990B2 (en) | 2004-03-31 | 2012-08-07 | E I Du Pont De Nemours And Company | Triarylamine compounds, compositions and uses therefor |
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