Long-term stable photoactive composition, such as phosphorescent composition or TTA-photon upconversion composition

1. A composition containing:

a) at least one compound capable of reacting with singlet oxygen, and

b) at least one compound, which has a triplet state capable of energy transfer via an emissive process or a non-emissive process, wherein the at least one compound having a triplet state is

i) at least one phosphorescent compound sufficiently soluble in the compound capable of reacting with singlet oxygen and/or

ii) at least one sensitizer compound being capable of absorbing radiation at a first frequency v 1 and at least one emissive compound, wherein the at least one sensitizer compound is capable of transferring energy to the at least one emissive compound and wherein the at least one emissive compound, after obtaining energy transferred from the at least one sensitizer compound, is capable of emitting light at a second frequency v 2 , wherein the following equation is fulfilled: v 2 >v 1 , wherein the at least one sensitizer compound is capable of a triplet-triplet energy transfer to the at least one emissive compound,

wherein the at least one compound capable of reacting with singlet oxygen comprises at least one terminal unsaturated carbon-carbon bond and is selected from the group consisting of compounds having anyone of the following general formulae (I) to (X):

wherein

X is O or S,

R is alkenyl or alkynyl and

R1 is H, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is O or S,

R is alkenyl or alkynyl,

Y is alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, aralkynyl, aryl or heteroaryl and

R1, R2, R3 are independently from each other H, XR, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkenyl, aralkynyl, aralkyl, aryl or heteroaryl, wherein X and R are as defined above,

wherein

X is N or P,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

PEG is an oligoethylene glycol or polyethylene glycol group having 2 to 99 ethylene glycol units,

R1 is alkenyl or alkynyl,

Y is Si and

R2 and R3 are independently from each other H, COOR, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl or XR4, wherein X is N, P or As and R, R4 are independently from each other alkenyl or alkynyl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1, R2 and R3 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

n, m and o are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more,

wherein

R is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n and m are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more

or

wherein

R and R1 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n is an integer between 1 and 20 and

p is an integer of 2 or more,

wherein the total concentration of all phosphorescent compounds is 1·10 −5 to 1·10 −3 mol/l, and wherein the total content of all phosphorescent compounds and all compounds comprising at least one terminal unsaturated carbon-carbon bond in the composition is at least 90 mol-%.

2. A composition containing:

a) at least one compound capable of reacting with singlet oxygen, and

b) at least one compound, which has a triplet state capable of energy transfer via an emissive process or a non-emissive process, wherein the at least one compound having a triplet state is

i) at least one phosphorescent compound sufficiently soluble in the compound capable of reacting with singlet oxygen and/or

ii) at least one sensitizer compound being capable of absorbing radiation at a first frequency v 1 and at least one emissive compound, wherein the at least one sensitizer compound is capable of transferring energy to the at least one emissive compound and wherein the at least one emissive compound, after obtaining energy transferred from the at least one sensitizer compound, is capable of emitting light at a second frequency v 2 , wherein the following equation is fulfilled: v 2 >v 1 , wherein the at least one sensitizer compound is capable of a triplet-triplet energy transfer to the at least one emissive compound,

wherein the at least one compound capable of reacting with singlet oxygen comprises at least one terminal unsaturated carbon-carbon bond and is selected from the group consisting of compounds having anyone of the following general formulae (I) to (X):

wherein

X is O or S,

R is alkenyl or alkynyl and

R1 is H, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is O or S,

R is alkenyl or alkynyl,

Y is alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, aralkynyl, aryl or heteroaryl and

R1, R2, R3 are independently from each other H, XR, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkenyl, aralkynyl, aralkyl, aryl or heteroaryl, wherein X and R are as defined above,

wherein

X is N or P,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

PEG is an oligoethylene glycol or polyethylene glycol group having 2 to 99 ethylene glycol units,

R1 is alkenyl or alkynyl,

Y is Si and

R2 and R3 are independently from each other H, COOR, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl or XR4, wherein X is N, P or As and R, R4 are independently from each other alkenyl or alkynyl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1, R2 and R3 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

n, m and o are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more,

wherein

R is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n and m are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more

or

wherein

R and R1 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n is an integer between 1 and 20 and

p is an integer of 2 or more,

wherein the total concentration of all sensitizer compounds is 1·10 −5 to 1·10 −3 mol/l, the total concentration of all emissive compounds is 1·10 −2 to 1·10 −4 mol/l and the total content of all sensitizer compounds, all emissive compounds and all compounds capable of reacting with singlet oxygen is at least 90 mol-%.

3. A composition containing:

a) at least one compound capable of reacting with singlet oxygen, and

b) at least one compound, which has a triplet state capable of energy transfer via an emissive process or a non-emissive process, wherein the at least one compound having a triplet state is

i) at least one phosphorescent compound sufficiently soluble in the compound capable of reacting with singlet oxygen and/or

ii) at least one sensitizer compound being capable of absorbing radiation at a first frequency v 1 and at least one emissive compound, wherein the at least one sensitizer compound is capable of transferring energy to the at least one emissive compound and wherein the at least one emissive compound, after obtaining energy transferred from the at least one sensitizer compound, is capable of emitting light at a second frequency v 2 , wherein the following equation is fulfilled: v 2 >v 1 , wherein the at least one sensitizer compound is capable of a triplet-triplet energy transfer to the at least one emissive compound,

wherein the at least one compound capable of reacting with singlet oxygen comprises at least one terminal unsaturated carbon-carbon bond and is selected from the group consisting of compounds having anyone of the following general formulae (I) to (X):

wherein

X is O or S,

R is alkenyl or alkynyl and

R1 is H, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is O or S,

R is alkenyl or alkynyl,

Y is alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, aralkynyl, aryl or heteroaryl and

R1, R2, R3 are independently from each other H, XR, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkenyl, aralkynyl, aralkyl, aryl or heteroaryl, wherein X and R are as defined above,

wherein

X is N or P,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

PEG is an oligoethylene glycol or polyethylene glycol group having 2 to 99 ethylene glycol units,

R1 is alkenyl or alkynyl,

Y is Si and

R2 and R3 are independently from each other H, COOR, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl or XR4, wherein X is N, P or As and R, R4 are independently from each other alkenyl or alkynyl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1, R2 and R3 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

n, m and o are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more,

wherein

R is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n and m are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more

or

wherein

R and R1 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n is an integer between 1 and 20 and

p is an integer of 2 or more,

wherein the at least one compound having a triplet state capable of energy transfer via an emissive process or a non-emissive process is i) at least one phosphorescent compound that can be sufficiently dissolved in the compound capable of reacting with singlet oxygen.

4. A composition containing:

a) at least one compound capable of reacting with singlet oxygen, and

b) at least one compound, which has a triplet state capable of energy transfer via an emissive process or a non-emissive process, wherein the at least one compound having a triplet state is

i) at least one phosphorescent compound sufficiently soluble in the compound capable of reacting with singlet oxygen and/or

ii) at least one sensitizer compound being capable of absorbing radiation at a first frequency v 1 and at least one emissive compound, wherein the at least one sensitizer compound is capable of transferring energy to the at least one emissive compound and wherein the at least one emissive compound, after obtaining energy transferred from the at least one sensitizer compound, is capable of emitting light at a second frequency v 2 , wherein the following equation is fulfilled: v 2 >v 1 , wherein the at least one sensitizer compound is capable of a triplet-triplet energy transfer to the at least one emissive compound,

wherein the at least one compound capable of reacting with singlet oxygen comprises at least one terminal unsaturated carbon-carbon bond and is selected from the group consisting of compounds having anyone of the following general formulae (I) to (X):

wherein

X is O or S,

R is alkenyl or alkynyl and

R1 is H, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is O or S,

R is alkenyl or alkynyl,

Y is alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, aralkynyl, aryl or heteroaryl and

R1, R2, R3 are independently from each other H, XR, alkyl, ether-alkyl, ether-alkenyl, alkenyl, alkynyl, aralkenyl, aralkynyl, aralkyl, aryl or heteroaryl, wherein X and R are as defined above,

wherein

X is N or P,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

PEG is an oligoethylene glycol or polyethylene glycol group having 2 to 99 ethylene glycol units,

R1 is alkenyl or alkynyl,

Y is Si and

R2 and R3 are independently from each other H, COOR, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl or XR4, wherein X is N, P or As and R, R4 are independently from each other alkenyl or alkynyl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1 and R2 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

X is P, S, B or Si,

R is alkenyl or alkynyl and

R1, R2 and R3 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

wherein

n, m and o are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more,

wherein

R is H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n and m are independently from each other an integer between 1 and 20 and

p is an integer of 2 or more

or

wherein

R and R1 are independently from each other H, alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl,

n is an integer between 1 and 20 and

p is an integer of 2 or more,

wherein the at least one compound having a triplet state capable of energy transfer via an emissive process or a non-emissive process is ii) at least one sensitizer compound being capable of absorbing radiation at a first frequency v 1 and at least one emissive compound, wherein the at least one sensitizer compound is capable of transferring energy to the at least one emissive compound and wherein the at least one emissive compound, after obtaining energy transferred from the at least one sensitizer compound, is capable of emitting light at a second frequency v 2 , wherein the following equation is fulfilled: v 2 >v 1 , wherein the at least one sensitizer compound is capable of a triplet-triplet energy transfer to the at least one emissive compound.

5. The composition in accordance with claim 4 , wherein the at least one emissive compound is capable of a triplet-triplet annihilation.

6. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen is contained in the composition in such an amount that the number of terminal unsaturated carbon-carbon bonds of the at least one compound capable of reacting with singlet oxygen is at least 100 times higher in the composition than the number of molecules of all compounds having a triplet state capable of energy transfer via an emissive process or a non-emissive process.

7. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (II), in which X is oxygen, R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl, Y is C 1-6 -alkyl or phenyl and R1, R2, R3 are independently from each other H and XR, wherein X is oxygen and R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

8. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen is selected from the group consisting of 3-butene-1-ol, 4-pentene-1-ol, 5-hexene-1-ol, 6-heptene-1-ol, 7-octene-1-ol, 1,2-di-(3-buten-1-yloxy)ethane, 1,2-di-(4-penten-1-yloxy)ethane, 1,2-di-(5-hexen-1-yloxy)ethane, 1,2-di-(6-hepten-1-yloxy)ethane, 1,2-di-(7-octen-1-yloxy)ethane, 1,2-di-(3-buten-1-yloxy)benzene, 1,2-di-(4-penten-1-yloxy)benzene, 1,2-di-(5-hexen-1-yloxy)benzene, 1,2-di-(6-hepten-1-yloxy)benzene, 1,2-di-(7-octen-1-yloxy)benzene, 1,3,5-tri-(3-buten-1-yloxy)benzene, 1,3,5-tri-(4-penten-1-yloxy)benzene, 1,3,5-tri-(5-hexen-1-yloxy)benzene, 1,3,5-tri-(6-hepten-1-yloxy)benzene, 1,3,5-tri-(7-octen-1-yloxy)benzene and arbitrary combinations of two or more of these compounds.

9. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (III), wherein X is phosphorus, R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl and R1 and R2 are independently from each other H or selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

10. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (IV), in which PEG is an oligoethylene glycol or polyethylene glycol group having 2 to 99 ethylene glycol units, R1 is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl, Y is Si and R2, R3 are independently from each other H, COOR, XR4 or alkenyl selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl, wherein X is N or P and R, R4 are independently from each other selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

11. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (VII), wherein X is S, R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl and R1 is C 3-8 -alkyl, phenyl or alkenyl selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

12. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (VI), wherein X is P, R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl and R1 and R2 are independently from each other C 3-8 -alkyl, phenyl or alkenyl selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

13. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (VIII), wherein X is B, R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl and R1 and R2 are independently from each other C 3-8 -alkyl, phenyl or alkenyl selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

14. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen has the general formula (IX), wherein X is Si, R is selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl and R1, R2 and R3 are independently from each other C 3-8 -alkyl, phenyl or alkenyl selected from the group consisting of allyl, 3-buten-1-yl, 4-penten-1-yl, 5-hexen-1-yl, 6-hepten-1-yl, 7-octen-1-yl, 8-nonen-1-yl, 9-decen-1-yl and 10-undecen-1-yl.

15. The composition in accordance with claim 4 , wherein the at least one compound capable of reacting with singlet oxygen is one according to the general formula (Xa), wherein n, m and o are independently from each other an integer between 1 and 10 and p is an integer of 2 to 120.

16. The composition in accordance with claim 15 , wherein the at least one compound capable of reacting with singlet oxygen is one according to the subsequent formulae (XI) to (XIV):

wherein in each of these formulae p is an integer of 2 to 120.