Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
1998-07-20
2003-04-08
Yamnitzky, Marie (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C428S446000, C428S447000, C428S448000, C313S504000, C313S506000, C528S033000, C528S034000, C528S038000, C528S043000
Reexamination Certificate
active
06544670
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a hole transporting polymer, a method of producing the same, and an organic electroluminescence device (hereinafter referred to as an “organic EL device”, sometimes) using the hole transporting polymer.
2. Description of the Related Art
An inorganic electroluminescence device (hereinafter referred to as an “inorganic EL device”, sometimes) using an inorganic fluorescent substance has hitherto been used for a flat light source as backlight, a display device such as flat panel display or the like, but a high-voltage alternating current was required for driving the devices.
Tang et al. have recently fabricated an organic EL device having a two-layer structure, comprising a laminate of a light emitting layer of an organic fluorescent dyes and a layer of an organic charge transporting compound generally used in a photosensitive layer for electrophotography (U.S. Pat. No. 4,539,507). Since the organic EL device has a feature that emission of various colors can be easily obtained, in addition to low-voltage driving and high luminance, in comparison with the inorganic EL device, various attempts have been made and reported regarding the development and improvement of the device structure, organic fluorescent dyes and organic charge transporting compounds, etc [Jpn. J. Appl. Phys. Vol. 27, page L269 (1988); and J. Appl. Phys., Vol. 65, page 3610 (1989)]
As the hole transporting material, for example, various compounds such as oxadiazole derivatives, oxazol derivatives, hydrazone derivatives, triarylpyrazoline derivatives, arylamine derivatives, stilbene derivatives and the like have been reported.
In case of using only a low molecular weight hole transporting material in the organic EL device, the mechanical strength and heat resistance of the hole transporting layer were insufficient. As the method of forming a hole transporting layer, deposition under vacuum is generally used but has a problem of high production cost. To the contrary, there have been reported a lot of examples using the hole transporting polymer, such as organic EL device using a polystyrene derivatives having an aromatic amine group on the side chain (JP-A-8-259935), organic EL device using a polyester having an aromatic amine group(JP-A-8-259880) and the like, for the purpose of improving the durability and film-forming property. However, these organic EL devices are not necessarily satisfactory in view of the stability on driving.
On the other hand, in a photosensitive layer for electrophotography using the hole transporting material, like the organic EL device, the addition of a polysiloxane is performed for the purpose of preventing deterioration caused by corona discharge. Furthermore, there has been reported a hole transporting polysiloxane obtained by mixing a silicon hole transporting material with a curable polysiloxane and curing the mixture for the purpose of imparting the hole transporting property to the polysiloxane (JP-A-9-124943).
As an example of using a hole transporting polysiloxane in an organic EL, an organic EL device obtained by mixing a polysiloxane having a carbazole group on the side chain with a light emitting polymer has been proposed (WO 9501871).
SUMMARY OF THE INVENTION
An object of the present invention is to provide a hole transporting polymer having excellent hole transporting property, excellent durability and excellent film-forming property, and a method of producing the same, and an organic EL device having excellent light emitting characteristics, using the hole transporting polymer.
The present inventors have intensively studied to solve these problems, and found that a specific novel hole transporting polymer has excellent hole transporting property, excellent durability and excellent film-forming property, and that an organic EL device prepared by using the hole transporting polymer has excellent light emitting characteristics. Thus, the present invention has been accomplished.
SUMMARY OF THE INVENTION
That is, the present invention relates to [1] a hole transporting polymer comprising a repeating structural unit represented by the following general formula (1), and having a polystyrene-reduced number-average molecular weight of from 10
3
to 10
7
:
wherein R
1
represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms; Ar
1
represents an arylene group having 6 to 30 carbon atoms, or an arylene ethenylene group represented by the following general formula (2); Ar
2
and Ar
3
independently represent an aryl group having 6 to 30 carbon atoms, an aromatic amine group represented by the following general formula (3), or an arylene ethenylene group represented by the following general formula (4); and a ring may be formed between Ar
1
and Ar
2
, or Ar
1
and Ar
3
, or Ar
2
and Ar
3
:
wherein Ar
4
and Ar
5
independently represent an arylene group having 6 to 30 carbon atoms; R
2
and R
3
independently represent hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms:
wherein Ar
6
represents an arylene group having 6 to 30 carbon atoms; R
4
and R
5
independently represent an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms; and a ring may be formed between Ar
6
and R
4
, or Ar
6
and R
5
, or R
4
and R
5
:
wherein Ar
7
represents an arylene group having 6 to 30 carbon atoms; R
6
and R
7
independently represent hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms; Ar
8
represents an aryl group having 6 to 30 carbon atoms.
The present invention also relates to [2] a hole transporting polymer comprising a repeating structural unit represented by the following general formula (5), and having a polystyrene-reduced number-average molecular weight of from 10
3
to 10
7
:
wherein Ar
9
and Ar
11
independently represent an arylene group having 6 to 30 carbon atoms, an aromatic amine group represented by the following general formula (6) or an arylene ethenylene group represented by the following general formula (7); Ar
10
represents an aryl group having 6 to 30 carbon atoms, an aromatic amine group represented by the following general formula (8) or an arylene ethenylene group represented by the following general formula (9); a ring may be formed between Ar
9
and Ar
10
, or Ar
9
and Ar
11
, or Ar
10
and Ar
11
; and R
8
, R
9
, R
10
and R
11
independently represent hydroxy group, an alkyl or alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms, a group represented by the following general formula (10) or (12), or divalent oxygen atom which may be bonded to an intramolecular silicon atom by crosslinking or to a silicon atom in the molecule vicinally sited by crosslinking:
wherein Ar
12
and Ar
13
independently represent an arylene group having 6 to 30 carbon atoms; R
12
represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms; and a ring may be formed between Ar
12
and Ar
13
, or Ar
12
and R
12
, or Ar
13
and R
12
:
wherein Ar
14
and Ar
15
independently represent an arylene group having 6 to 30 carbon atoms; and R
13
and R
14
independently represent hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 32 carbon atoms
Kitano Makoto
Noguchi Takanobu
Ohnishi Toshihiro
Osada Takenori
Yamaguchi Fumi
Fitch Even Tabin & Flannery
Sumitomo Chemical Company Ltd.
Yamnitzky Marie
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