Organic electroluminescence device
First Claim
1. In an organic electroluminescence device, which comprises a light emitting layer, the improvement comprising said light emitting layer comprising a dimerized styryl compound of the formula (a):
- ##STR85## wherein D and D'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'),E, E'"'"', F, F'"'"', G and G'"'"' are the same or different from each other and are each a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, a cyclohexyl group, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'), or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms which is unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'), with the proviso that F and G are not both hydrogen atoms, and F'"'"' and G'"'"' are not both hydrogen atoms;
the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, halogen atoms, a carboxyl group, an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group;
E and D, or E'"'"'and D'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring, F and G, or F'"'"' and G'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring; and
Q is a divalent group to break the conjunction.
1 Assignment
0 Petitions
Accused Products
Abstract
An electroluminescence device (organic EL device) which comprises a pair of electrodes with an emitting layer therebetween. The emitting layer contains a dimerized styryl compound of the formula ##STR1## wherein D and D'"'"' are each an arylene group or a divalent aromatic heterocyclic group, E, E'"'"', F, F'"'"' G and G'"'"' are each a hydrogen, an aryl group, an alkyl group, an aralkyl group, an alkoxyl group or a monovalent aromatic heterocyclic group and Q is a divalent group which breaks the conjugation. The dimerized styryl compound has a desirable light emitting efficiency which serves to increase the molecular weight to improve the thin film property. The organic EL device of the present invention is useful in preparing display devices.
-
Citations
28 Claims
-
1. In an organic electroluminescence device, which comprises a light emitting layer, the improvement comprising said light emitting layer comprising a dimerized styryl compound of the formula (a):
- ##STR85## wherein D and D'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'),
E, E'"'"', F, F'"'"', G and G'"'"' are the same or different from each other and are each a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, a cyclohexyl group, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'), or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms which is unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'), with the proviso that F and G are not both hydrogen atoms, and F'"'"' and G'"'"' are not both hydrogen atoms; the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, halogen atoms, a carboxyl group, an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group; E and D, or E'"'"'and D'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring, F and G, or F'"'"' and G'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring; and Q is a divalent group to break the conjunction. - View Dependent Claims (3, 13, 18, 20, 22, 26, 27, 28)
- ##STR85## wherein D and D'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'),
-
2. In an organic electroluminescence device, which comprises a light emitting layer, the improvement comprising said light emitting layer comprising a dimerized styryl compound of the formula (b):
- ##STR86## wherein J, J'"'"', L and L'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"');
K, K'"'"', M, M'"'"', N and N'"'"' are the same or different from each other and are each a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, a cyclohexyl group, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'), with the proviso that M and N are not both hydrogen atoms, and M'"'"' and N'"'"' are not both hydrogen atoms; the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, a halogen atom, a carboxyl group, an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group; K and J, or K'"'"' and J'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring;
M and N, or M'"'"' and N'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring; andQ is a divalent group to break the conjunction. - View Dependent Claims (12, 14, 15, 16, 17, 19, 21, 23)
- ##STR86## wherein J, J'"'"', L and L'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"');
-
4. In an organic electroluminescence device which comprises an emitting layer, the improvement which comprises said emitting layer comprising an oligomer compound containing a styryl compound of the formula (c):
- ##STR87## wherein J and L are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'),
K is a hydrogen atom or an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms or a monovalent aromatic heterocyclic group having 3 to 20carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'), the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an acyl group having 1 to6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, a halogen atom, a carboxyl group, an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group;
Q is a divalent group to break the conjugation; andn is 1 to 5. - View Dependent Claims (24)
- ##STR87## wherein J and L are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'),
-
5. A dimerized styryl compound of the formula (a):
- ##STR88## wherein D and D'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'),
E, E'"'"', G and G'"'"' are the same or different from each other and are each a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, a cyclohexyl group, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituent (a'"'"'); F and F'"'"' are the same or different from each other and are each an aryl group having 6 to 20 carbon atoms, cyclohexyl group, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'); the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxyl group;
having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, a halogen atom, a carboxyl group, an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group;E and D, or E'"'"' and D'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring, F and G, or F'"'"' and G'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring; and Q is a divalent group to break the conjunction. - View Dependent Claims (7, 10)
- ##STR88## wherein D and D'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or are mono-substituted or poly-substituted with substituents (a'"'"'),
-
6. A dimerized styryl compound of the formula (b):
- ##STR89## wherein J, J'"'"', L and L'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"');
K, K'"'"', M, M'"'"', N and N'"'"' are the same or different from each other and are each a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, a cyclohexyl group, an alkyl group having 1 to 10 carbon atoms, or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'), with the proviso M and N are not both hydrogen atoms, and M'"'"' and N'"'"' are not both hydrogen atoms; the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, a halogen atom, a carboxyl group, an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group; K and J, or K'"'"' and J'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring;
M and N, or M'"'"' and N'"'"' may combine with each other to form a saturated or unsaturated five-membered or six-membered ring; andQ is a divalent group to break the conjunction. - View Dependent Claims (8, 11)
- ##STR89## wherein J, J'"'"', L and L'"'"' are the same or different from each other and are each an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"');
-
9. An oligomer compound of the formula (c):
- ##STR92## wherein J and L are the same or different and each other and are an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'),
K is a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'), M and N are the same or different from each other and are each a hydrogen atom, or an aryl group having 6 to 20 carbon atoms, a cyclohexyl group, an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms or a monovalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted by substituents (a'"'"') or poly-substituted by substituents (a'"'"'), the substituents (a'"'"') are an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkoxy-carbonyl group having 2 to 7 carbon atoms, an aryloxy-carbonyl group having 7 to 21 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, an acylamino group having 1 to 6 carbon atoms, a halogen atom, a carboxyl group an amino-carbonyl group, a hydroxyl group, a cyano group, a nitro group, or an amino group; and Q is a divalent group to break the conjugation and wherein n is 1 to 5.
- ##STR92## wherein J and L are the same or different and each other and are an arylene group having 6 to 20 carbon atoms or a divalent aromatic heterocyclic group having 3 to 20 carbon atoms, which are unsubstituted or mono-substituted or poly-substituted with substituents (a'"'"'),
-
25. An organic electroluminescence device comprising a light emitting layer disposed between a pair of electrodes, the light emitting layer comprising a dimerized styryl compound selected from the group consisting of ##STR96## ##STR97## wherein t-Bu is tertiarybutyl.
Specification