JP2005068068A5

JP2005068068A5 - Organic compounds having m-linked aromatic 6-membered rings

Info

Publication number: JP2005068068A5
Application number: JP2003299512A
Authority: JP
Filing date: 2003-08-25
Publication date: 2006-04-13
Anticipated expiration: 2023-08-25

Description

即ち本発明の要旨は、ａ個（ａは３以上の整数）の芳香族６員環がｍ−連結している基本骨格（但し、この基本骨格が環上に３個の芳香族６員環がｍ−結合している芳香環を有する場合には、当該環の少なくとも一つは含窒素芳香族６員環である）を有し、かつこの骨格上に、ｂ個（ｂは１以上で（ａ＋２）以下の整数）の−ＮＲ¹Ｒ²基（Ｒ¹およ
びＲ²は、各々独立に任意の置換基）を有し、該−ＮＲ¹Ｒ²基がいずれも、芳香族６員環
におけるｍ−連結部位に対して、ｍ−位に結合していることを特徴とする、有機化合物（但し、芳香族６員環は−ＮＲ¹Ｒ²基以外の置換基を有していてもよく、１分子中に含まれる複数の芳香族６員環は、互いに同一であっても異なっていてもよい。また、１分子中に含まれる複数の−ＮＲ¹Ｒ²基は、互いに同一であっても異なっていてもよい。）に存する。
That is, the gist of the present invention is that a basic skeleton in which a 6 (a is an integer of 3 or more) aromatic 6-membered rings are m-linked (provided that the basic skeleton has 3 aromatic 6-membered rings on the ring). Has an m-bonded aromatic ring, at least one of the rings is a nitrogen-containing aromatic 6-membered ring), and b (b is 1 or more) on this skeleton. (A + 2) or less) -NR ¹ R ² group (R ¹ and R ² are each independently an arbitrary substituent), and each of the —NR ¹ R ² groups is an aromatic 6-membered ring An organic compound characterized in that it is bonded to the m-position with respect to the m-linkage site in the formula (provided that the aromatic 6-membered ring may have a substituent other than the —NR ¹ R ² group) well, more aromatic 6-membered ring contained in one molecule may being the same or different. a plurality of -NR ¹ R ² groups contained in one molecule, It is in may be the same or different.) To exist.

上記例示した基本骨格の中でも、
・薄膜を形成したときの製膜性がとりわけ優れていること、
・溶解性に優れているため、湿式製膜法にも適していること、
・分子骨格を出来る限り単純なユニットによって形成することにより、電気的な酸化や還元を受けた際、分子内での電子や正孔の局在化現象、即ち、電気的応力集中を生じにくくし、繰返し電気化学的酸化還元に対する耐久性を飛躍的に向上させることができること、・ベンゼン環を環Ａとしたことにより、適度に広い酸化還元電位差を持たせることができること
などの理由から、ＡＳ−１〜５，７，１４〜１７，１９，２０がより好ましく、ＡＳ−１〜５，７が更に好ましい。
Among the basic skeletons exemplified above,
・ The film-forming property when a thin film is formed is particularly excellent.
・ Since it has excellent solubility, it is also suitable for wet film formation.
-By forming the molecular skeleton with as simple a unit as possible, when subjected to electrical oxidation or reduction, the phenomenon of localization of electrons and holes in the molecule, that is, electrical stress concentration is less likely to occur. AS- 1-5, 7, 14 ～17,19,20 more preferably, AS-1~5,7 is more preferable.

引続き、発光層５として、実施例１で得られた本発明化合物および本文中に（Ｔ−２）で示したイリジウム錯体を別々のセラミックるつぼに設置し、２元同時蒸着法により成膜を行った。
Subsequently, the compound of the present invention obtained in Example 1 and the iridium complex indicated by (T-2) in the text were placed in separate ceramic crucibles as the light-emitting layer 5 and film formation was performed by the binary co-evaporation method. It was.

Claims

A basic skeleton in which a ( 6 is an integer of 3 or more) aromatic 6-membered rings are m-linked (however, this basic skeleton has m-linked 3 aromatic 6-membered rings on the ring) In the case of having an aromatic ring, at least one of the rings is a nitrogen-containing aromatic 6-member), and b (b is an integer of 1 to (a + 2)) on this skeleton -NR ¹ R ² group (R ¹ and R ² are optional substituents independently) have, both -NR ¹ R ² groups, with respect m- ligation site in the aromatic 6-membered ring, An organic compound which is bonded to the m-position. (However, the aromatic 6-membered ring may have a substituent other than the —NR ¹ R ² group, and the plurality of aromatic 6-membered rings contained in one molecule may be the same or different from each other. In addition, a plurality of —NR ¹ R ² groups contained in one molecule may be the same as or different from each other.

The organic compound according to claim 1 , characterized in that each of the a 6 aromatic 6-membered rings has 1 or 0 -NR ¹ R ² groups.

R ¹¹ And R ²² Is an aromatic hydrocarbon group which may have a substituent each independently, The organic compound of Claim 1 or 2 characterized by the above-mentioned.

The 9-carbazolyl group in which —NR ¹ R ² group may have a substituent on the ring

And characterized in that, the organic compound according to claim 1 or 2.

An organic compound represented by the general formula (1).

(In the formula, ring A ⁰ represents an aromatic 6-membered ring which may have a substituent other than —X , and X represents an NR ¹ R ² group (R ¹ and R ² are optional substituents). . n is table an integer of 1 to 6, c, d and e it
Each independently represents 0 or 1 . However, A ⁰ and X contained in one molecule each represent the same thing. )

R ¹¹ And R ²² 6. The organic compound according to claim 5, wherein each is independently an aromatic hydrocarbon group which may have a substituent.

9-carbazolyl group in which —X may have a substituent on the ring

The organic compound according to claim 5, wherein

An organic compound represented by the general formula (2).

Wherein ring A ⁰ represents the same aromatic 6-membered ring optionally having a substituent other than —X,
ring
9-carbazolyl group which may have a substituent on

Represents. n represents an integer of 1 to 6. )

An organic compound represented by the following formula.