Compositions – Organic luminescent material containing compositions
Reexamination Certificate
2000-06-30
2001-10-09
Koslow, C. Melissa (Department: 1755)
Compositions
Organic luminescent material containing compositions
C726S006000, C313S504000
Reexamination Certificate
active
06299796
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a styryl compound, a method for the preparation thereof, and an electroluminescent (EL) element comprising the same.
BACKGROUND OF THE INVENTION
Recently, investigation and development on various display elements have been actively made. Among others, organic electroluminescent (EL) elements are being watched as promising display elements since they can emit high-luminance luminescence at a low driving voltage. For instance, an organic EL element having a thin layer formed by vapor deposition of an organic compound is known as described in
Applied Physics Letters
, Vol. 51, page 913 (1987). The organic EL element described therein has a laminated layer structure of an electron-transporting material and a hole-transporting material, and its luminescent characteristics are greatly improved in comparison with conventional EL elements of single layer type.
In order to improve luminescent efficiency of the EL element of laminated type described above, a method of doping a fluorescent dye is known. For example, an organic EL element doped with a coumarin dye described in
Journal of Applied Physics
, Vol. 65, page 3610 (1989) exhibits remarkably improved luminescent efficiency as compared with an organic EL element without doping (non-doped type element). However, the doped element is inferior in production aptitude, for example, because it is necessary to control the dope amount subtly. Accordingly, it was desired to develop a non-doped type element that emits highly efficiently.
In the field of organic EL elements, color of luminescence requested may be varied and it is possible to obtain light having the desired wavelength by changing the kind of fluorescent dye to be employed.
However, only a small number of fluorescent dyes emitting blue to blue-green light which emits highly efficiently light having the desired wavelength and have good durability are known, and a further development has been desired.
SUMMARY OF THE INVENTION
Objects of the present invention are to provide a compound which emits light having a wavelength in a blue to blue-green region and has excellent durability, a method for the preparation thereof, and an electroluminescent element containing the same.
Other objects of the present invention will become apparent from the following description and examples.
The above described objects of the present invention are accomplished by the following.
(A) An electroluminescent element comprising at least one compound containing at least one unit represented by formula (1):
wherein X
1
represents an oxygen atom, a sulfur atom or >NR
6
; R
2
, R
3
, R
4
, R
5
and R
6
, which are the same or different, each represents a hydrogen atom or a substituent, provided that at least one of R
2
, R
3
, R
4
and R
5
represents an aromatic group; R
a
and R
b
, which are the same or different, each represents a hydrogen atom or a substituent; Ar
1
represents an aromatic linking group; and Ar
2
and Ar
3
each represents an aromatic group.
(B) An electroluminescent element as described in (A) wherein, in formula (1), R
3
is an aryl group, and R
a
and R
b
each represents a hydrogen atom.
(C) An electroluminescent element as described in (A), wherein, in formula (1), R
4
is an aryl group, and R
a
and R
b
each represents a hydrogen atom.
(D) A high molecular weight compound comprising a partial skeleton represented by formula (2) in the polymer main chain:
wherein X
2
represents an oxygen atom, a sulfur atom or >NR
16
; R
12
, R
13
, R
14
, R
15
and R
16
, which are the same or different, each represents a hydrogen atom or a substituent, provided that at least one of R
12
, R
13
, R
14
, R
15
and R
16
represents an aromatic group; R
c
and R
d
, which are the same or different, each represents a hydrogen atom or a substituent; and Ar
4
represents an aromatic group.
(E) An electroluminescent element comprising at least one high molecular weight compound comprising a partial skeleton represented by formula (2) in the polymer main chain, as described in (D).
(F) An electroluminescent element as described in (A), (B), (C) or (E), which is non-doped type.
DETAILED DESCRIPTION OF THE INVENTION
The compound containing at least one unit represented by the formula (1) will be described in greater detail below.
In the formula (1), X
1
represents an oxygen atom, a sulfur atom or >NR
6
wherein R
6
represents a hydrogen atom or a substituent. Examples of the substituent represented by R
6
include an alkyl group (having preferably from 1 to 20, more preferably from 1 to 12, particularly preferably from 1 to 8 carbon atom, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), an alkenyl group (having preferably from 2 to 20, more preferably from 2 to 12, particularly preferably from 2 to 8 carbon atoms, e.g., vinyl, allyl, 2-butenyl, and 3-pentenyl), an alkynyl group (having preferably from 2 to 20, more preferably from 2 to 12, particularly preferably from 2 to 8 carbon atoms, e. g., propargyl and 3-pentynyl), an aryl group (having preferably from 6 to 30, more preferably from 6 to 20, particularly preferably from 6 to 12 carbon atoms, e.g., phenyl, p-methylphenyl, and naphthyl), a substituted carbonyl group (having preferably from 1 to 40, more preferably from 1 to 20, more preferably from 1 to 12 carbon atoms, e.g., acetyl, benzoyl, methoxycarbonyl, dimethyl-aminocarbonyl, and phenylaminocarbonyl), a substituted sulfonyl group (having preferably from 1 to 20, more preferably from 1 to 16, particularly preferably from 1 to 12 carbon atoms, e.g., mesyl, and tosyl) and a heterocyclic group (which contains one or more-hetero atoms, for example, a nitrogen atom, an oxygen atom and a sulfur atom and has preferably from 1 to 20, more preferably from 1 to 16, particularly preferably from 1 to 12 carbon atoms, e.g., imidazolyl, pyridyl, furyl, and piperidyl). These substituents may be further substituted. R
6
is preferably a hydrogen atom, an alkyl group or an aryl group, and particularly preferably a hydrogen atom or an alkyl group.
X
1
is preferably an oxygen atom or a sulfur atom, and particularly preferably an oxygen atom.
Ar
1
represents an aromatic linking group, and Ar
2
and Ar
3
each represents an aromatic group. Examples of Ar
1
include an arylene group (preferably having 6 to 50 carbon atoms, more preferably having 6 to 30 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example, phenylene group, naphthylene group, anthrylene group), and a heteroarylene group (preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, pyridylene group, quinolylene group, thienylene group, carbazolylene group, oxadiazolylene group). These groups may be further substituted.
Examples of Ar
2
and Ar
3
include an aryl group (preferably having 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example, phenyl group, naphthyl group, anthryl group) and an aromatic heterocyclic group (preferably having 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, pyridyl group, quinolyl group, thienyl group, carbazolyl group, oxadiazolyl group). These groups may be further substituted.
Ar
1
is preferably a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted phenylene, naphthylene or anthrylene group, particularly preferably a substituted or unsubstituted phenylene group.
Ar
2
and Ar
3
each preferably represents a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, pyrenyl group, particularly preferably a substituted or unsubstituted naphthyl, anthryl, phenanthryl or pyrenyl group. R
2
, R
3
, R
4
and R
5
, which may be the same or different, each represents a hydrogen atom or a substituent, and at least one of R
2
, R
3
, R
4
and R
5
represents an
Fuji Photo Film Co. , Ltd.
Koslow C. Melissa
Sughrue Mion Zinn Macpeak & Seas, PLLC
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