Triptycene derivatives and their use for opto-electronics...

Details Triptycene derivatives and their use for opto-electronics... Triptycene derivatives and their use for opto-electronics...

2000-08-04

2003-01-21

Jones, Deborah (Department: 1775)

Stock material or miscellaneous articles

Composite

Of inorganic material

C428S917000, C428S704000, C313S504000, C313S506000, C252S301350, C257S040000, C257S103000

Reexamination Certificate

active

06509110

ABSTRACT:

DESCRIPTION
Triptycene derivatives, and their use for optoelectronic applications, in particular as electroluminescent materials
There is a considerable industrial demand for large-area solid-state light sources for a number of applications, predominantly in the area of display elements, display screen technology and illumination technology. The requirements made of these light sources can currently not be met entirely satisfactorily by any of the existing technologies.
As an alternative to conventional display elements, such as incandescent lamps, gas-discharge lamps and non-self-illuminating liquid-crystal display elements, electroluminescent (EL) materials and devices, such as light-emitting diodes (LEDs), have already been known for some time.
Electroluminescent materials are substances which are capable of emitting light on application of an electric field. The physical model for describing this effect is based on the recombination of electrons and electron holes, with emission of light. In light-emitting diodes, the charge carriers are injected into the electroluminescent material via the negative electrode or positive electrode. Electroluminescent devices contain a luminescent material as light-emitting layer. Electroluminescent materials and devices have been described in general terms, for example, in Ullmann's Encyclopedia of Industrial Chemistry, Vol. A9, 5th Ed., VCH Verlag, 1987 and the references cited therein. Besides inorganic substances, such as ZnS/Mn or GaAs, organic compounds have also been disclosed as EL materials.
A description of EL devices containing low-molecular-weight organic EL materials is given, for example, in U.S. Pat. No. 4,539,507.
Although good results have been achieved using such materials, the property profile of such compounds leaves plenty of room for improvement.
Since, in addition, the development of electroluminescent materials can in no way be regarded as complete, the manufacturers of illumination and display devices continue to be interested in a very wide variety of electroluminescent materials for such devices.
One of the reasons for this is that only the interaction of the electroluminescent material with the other components of the devices allows conclusions to be drawn on the suitability of the electroluminescent material too.
The object of the present invention was therefore to provide novel electroluminescent materials which, on use in illumination or display devices, are suitable for improving the property profile of these devices.
Surprisingly, it has now been found that certain derivatives of triptycene are particularly suitable for use as electroluminescent materials.
The invention therefore relates to the use of a triptycene derivative of the formula (I) in electroluminescent devices,
where the symbols in the formula have the following meanings:
K
1
, K
2
and K
3
are identical or different and are mono- or polycyclic systems, which may, if desired, contain heteroatoms, preferably N, S and/or O, and are substituted or unsubstituted;
X and Y are identical or different and are CR
1
, N, P, As or SiR
2
;
R
1
are identical or different and are H, halogen, pseudohalogen or a hydrocarbon radical having 1 to 30 carbon atoms, which may also, if desired, contain heteroatoms, preferably —O—, —N— and/or —S—;
R
2
are identical or different and are a hydrocarbon radical having 1 to 30 carbon atoms, which may also, if desired, contain heteroatoms, preferably —O—, —N— and/or —S—.
Compounds of the formula (I) are distinguished by adequate to good solubility in common organic solvents, good film-forming properties and a reduced tendency toward crystallization. The production of electroluminescent devices is thus simplified and their life extended. The emission properties of the compounds employed in accordance with the invention can be adjusted over the entire range of the visible spectrum through the choice of suitable substituents. In addition, the covalently bonded arrangement of the various parts of the triptycene compound allows a molecular structure such that certain properties can be set independently in different parts of the molecule. Thus, one part can have, for example, charge-transport or charge-injection properties, while the other has light-emitting properties.
At least one of the systems K
1-3
is preferably a fluorophore. For the purposes of the invention, a fluorophore is an atomic group which imparts fluorescence on the triptycene derivative, for example an extended aromatic system.
It is furthermore preferred for all three systems K
1-3
to be conjugated. Preferred, substituted or unsubstituted and/or bicyclic or polycyclic conjugated systems are:
where Q═S, O or NR
2
.
Particularly preferred compounds of the general formula (I) are triptycene derivatives of the formula (II) and of the formula (III)
where the symbols and indices have the following meanings:
X, Y, U and V are identical or different and are CR
1
, N, P, As or SiR
2
;
R
1
are identical or different and are H, halogen, pseudohalogen or a hydrocarbon radical having 1 to 30 carbon atoms, which may also, if desired, contain heteroatoms, preferably —O—, —N— and/or —S—;
R
2
are identical or different and are a hydrocarbon radical having 1 to 30 carbon atoms, which may also, if desired, contain heteroatoms, preferably —O—, —N— and/or —S—.
R
3
are identical or different and are, F, Cl, Br, I, CN, NO
2
, a branched or unbranched alkyl group having 1 to 22 carbon atoms, where one or more —CH
2
— groups may be replaced by —O—, —S—, —SO
3
—, —O—CO—, —CO—O—, aryl or heteroaryl (in each case having 4 to 10 carbon atoms), with the proviso that two oxygen atoms cannot be bonded directly to one another, and where one, more or all H atoms may be replaced by F, and where two substituents R
2
on the same ring may be linked to one another to form a ring or a further fused ring system or may also be hydrogenated, if desired partially, and may carry substituents, preferably of the type R
1
, with the proviso that the number of substituents is not greater than the total number of carbon atoms;
n are identical or different and are 0, 1, 2, 3, 4 or 5;
A and B are identical or different and are groups of the formula
(—M)
a
(—E)
b
(—M)
c
—(—E)
d
(—M)
e
(—E)
f
(—M)
g
(—E)
h
—R
4
where the symbols and indices have the following meanings:
M are identical or different and are —CR
5
═CR
6
, —C≡C—, —CR
7
═N— or —N═CR
7
—;
E are identical or different and are pyrazine-2,5-diyl, pyridazine-3,6-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3,4-thiadiazole-2,5-diyl, 1,3-thiazole-2,4-diyl, 1,3-thiazole-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl or naphthalene-1,5-diyl, in which one or two CH groups may be replaced by N, 1,3-oxazole-2,4-diyl, 1,3-oxazole-2,5-diyl, 1,3,4-oxadiazole-2,5-diyl, 4,4′-bi-phenylene, anthracenediyl, carbazolediyl, benzoxazolediyl, indene-2,5-diyl or indene-2,6-diyl, where one or more H atoms in the ring systems may be substituted by radicals R
8
;
R
4
, R
5
, R
6
and R
7
are identical or different and are
a) hydrogen, —F, —Cl, —CF
3
, —CN or NR
9
R
10
,
b) a straight-chain or branched alkyl radical (with or without an asymmetrical carbon atom) having 1 to 20 carbon atoms, where
b1) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH
3
)
2
—, and/or
b2) one or more CH
2
groups may be replaced by —CH═CH—, —C≡—C—, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene, and/or
b3) one or more H atoms may be replaced by F, CN and/or Cl;
R
8
are identical or different and are
a) —F, —Cl, —CF
3
, —CN or NO
2
b) a straight-chain or branched alkyl radical (with or without an asymmetrical carbon atom) having 1 to 20 carbon atoms, where
b1) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —NH—, N(C
1
-C
10
-alkyl), —N-phenyl-, —N-tolyl-, —N(C
2
H
5
—OCH
3
)— or —Si(CH
3
)
2
—, and/or
b2) one or more CH
2

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