Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2003-02-14
2004-07-20
Thompson, Camie S. (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C549S001000, C549S013000, C549S014000, C549S015000, C549S029000, C549S030000, C549S031000, C549S035000, C313S504000, C313S506000
Reexamination Certificate
active
06764777
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a novel, disc-like, sulfur-containing compound usable as functional materials such as light-emitting device materials, discotic liquid crystal materials, organic conductive materials (electrically conductive charge-transporting complexes, electrically conductive radical salts, etc.), organic ferromagnetic materials, etc., and a light-emitting device using the compound.
BACKGROUND OF THE INVENTION
Organic conductive materials have been researched and developed actively in recent years because they are light in weight and excellent in corrosion resistance, etc. unlike metal materials such as gold, silver and copper, and electrically conductive metal oxide materials such as ITO. Known as high-conductive, organic materials are most of charge-transporting complexes and radical cation salts, which are derived from electron-donating compounds having a 1,3-dithiol ring with a typical example of tetrathiafulvalene (TTF), and various electron-accepting compounds or inorganic anions.
It is known that discotic liquid crystals can be used as charge-transporting materials in various devices. For example, Adam, et al. reported that triphenylene-based, discotic liquid crystalline phase exhibited mobility of 10
−3
to 10
−2
cm
2
/Vs (Nature, Vol. 371, Page 141). Also disclosed are examples of using the discotic liquid crystals for such devices as organic electroluminescence (EL) devices.
Organic ferromagnetic materials have been actively researched for use in place of metal magnets such as iron-based magnets, etc. Reported by Breslow, R. is that in a charge-transporting complex derived from a dication of donor molecule and a dianion of acceptor molecule, one molecule is stably in a triplet ground state with parallel spins to provide ferromagnetic interaction (Pure and Applied Chemistry, Vol. 54, page 927, 1982). According to the group theory, a molecule with symmetry of C
3
or more or D
2d
has a degenerate molecular orbital and can be converted into the triplet ground state. Therefore, various high-symmetry molecules have been developed to synthesize ferromagnetic substances.
However, the organic conductive materials, the charge-transporting liquid crystals and the organic ferromagnetic materials mentioned above fail to show sufficient performance for industrial use.
Research and development are recently active worldwide to provide various light-emitting devices. Among others, organic electroluminescence (EL) devices are advantageous in that they are extremely thin, light in weight, rapid in response, wide in viewing angle, low in driving voltage, etc., thereby attracting much attention as a promising light-emitting device. Although various materials have been evaluated as components for the light-emitting devices to develop highly efficient devices with external quantum efficiency of more than 10%, they are still insufficient in durability and need a high driving voltage.
JP 11-111462 A discloses a light-emitting device comprising a compound with a dithiol ring, but it is different in structure from the compound of the present invention.
OBJECTS OF THE INVENTION
Accordingly, an object of the present invention is to provide a novel, disc-like, sulfur-containing compound having charge transportability and electron-donating properties.
Another object of the present invention is to provide a light-emitting device excellent in durability, which can be driven at a low driving voltage.
SUMMARY OF THE INVENTION
The compound according to the present invention has a chemical structure represented by the general formula (I):
wherein each of R
1
to R
12
and R
A1
to R
A6
represents a hydrogen atom or a substituent group, and adjacent groups of R
1
to R
12
and R
A1
to R
A6
may be bonded to each other to form a ring.
The compound of the present invention is preferably has a chemical structure represented by the general formula (II):
wherein each of R
1
to R
12
and R
B1
to R
B12
represents a hydrogen atom or a substituent group.
The light-emitting device according to the present invention comprises a pair of electrodes and one or more organic layers comprising a light-emitting layer disposed therebetween, at least one of the organic layers comprising at least one compound represented by the general formula (I) or (II).
In the light-emitting device of the present invention, at least one of the organic layers is preferably a layer having at least one compound represented by the general formula (I) or (II) dispersed in a polymer.
Each of R
1
, R
4
, R
5
, R
8
, R
9
and R
12
is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom. Each of R
2
, R
3
, R
6
, R
7
, R
10
and R
11
is preferably a hydrogen atom, an alkyl group, an alkylthio group, an alkyloxy group, a cyano group, alkyloxy group or a halogen atom, more preferably a hydrogen atom, an alkyl group or an alkylthio group. Each of R
A1
to R
A6
is preferably a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, a cyano group or halogen atoms, more preferably a hydrogen atom, alkyl group or alkylthio group. Each of R
B1
to R
B12
is preferably a hydrogen atom or an alkyl group.
At least one organic layer in the light-emitting device preferably further comprises a polymer. The above at least one organic layer is preferably a hole-injecting layer or a hole-transporting layer.
The amount of the compound represented by the formula (I) or (II) in a hole-injecting layer or a hole-transporting layer is preferably from 10 to 100% by weight, more preferably from 50 to 100% by weight. The amount of the compound represented by the formula (I) or (II) in the other layers except a hole-injecting layer or a hole-transporting layer is preferably from 5 to 90% by weight, more preferably from 5 to 50% by weight.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[1] Sulfur-containing Compound
In the general formula (I), each of R
1
to R
12
and R
A1
to R
A6
represents a hydrogen atom or a substituent group, and may be the same or different. Examples of the substituent groups represented by R
1
to R
12
and R
A1
to R
A6
include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy groups, aryloxycarbonyloxy groups, an amino group, acylamino groups, aminocarbonylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfamoylamino groups, alkylsulfonylamino groups, arylsulfonylamino groups, mercapto groups, alkylthio groups, arylthio groups, heterocyclic thio groups, sulfamoyl groups, a sulfo group, alkylsulfinyl groups, arylsulfinyl groups, alkylsulfonyl groups, arylsulfonyl groups, acyl groups, aryloxycarbonyl groups, alkoxycarbonyl groups, a carbamoyl group, arylazo groups, heterocyclic azo groups, imide groups, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group and silyl groups. The adjacent groups of R
1
to R
12
and R
A1
to R
A6
may be bonded to each other to form a ring, if possible.
Each of R
1
, R
4
, R
5
, R
8
, R
9
and R
12
is preferably a hydrogen atom or an alkyl group and particularly a hydrogen atom. The above alkyl group is a group preferably with 1 to 3 carbon atoms, more preferably with 1 or 2 carbon atoms, particularly a methyl group.
In a case where the compound represented by the general formula (I) is used as a liquid crystal material, preferred examples of R
2
, R
3
, R
6
, R
7
, R
10
and R
11
include alkyl groups, the number of carbon atoms thereof being preferably 2 to 30, more preferably 2 to 20, which may be unsubstituted alkyl groups such as an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group and an eicosyl group; or substituted alkyl groups such as a 4-methoxybutyl group and a 6-methoxyhexyl group; alky
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