Cyclic siloxane compound, organic electroluminescence device, and use of the same

1. A cyclic siloxane compound represented by Formula (1) below:

wherein, in Formula (1), R 1 and R 2 are each independently a luminescent monovalent group, a charge-transporting monovalent group, or another substituent; at least one of R 1 and R 2 is the luminescent monovalent group; and at least one of R 1 and R 2 is the charge-transporting monovalent group; and n is an integer of 2 to 100,

wherein the luminescent monovalent group is obtained by substituting a hydrogen atom of a phosphorescent compound represented by any one of Formulae (E-1) to (E-49) below with a linking group X A ; X A is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and the luminescent monovalent group is linked to a Si atom in Formula (1) via the linking group X A ;

the charge-transporting monovalent group is obtained by substituting a hydrogen atom of a charge-transporting compound represented by any one of Formulae (E-50) to (E-67) below with a linking group X B , and is linked to a Si atom in Formula (1) via the linking group X B ; X B is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and

the another substituent group is selected from the group consisting of aryl groups having 6 to 60 carbon atoms, monovalent heterocyclic groups, alkyl groups having 1 to 20 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms and aryloxyalkyl groups having 7 to 60 carbon atoms:

2. The cyclic siloxane compound according to claim 1 , wherein the group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20, is a group represented by —CH 2 —CH 2 —.

3. The cyclic siloxane compound according to claim 1 , wherein at least one of R 1 and R 2 in Formula (1) is a group obtained by substituting a hydrogen atom of a triarylamine derivative with a linking group X, and is linked to a Si atom in Formula (1) via the linking group X.

4. The cyclic siloxane compound according to claim 1 , wherein at least one of R 1 and R 2 in Formula (1) is a group obtained by substituting a hydrogen atom of a triarylborane derivative with a linking group X, and is linked to a Si atom in Formula (1) via the linking group X.

5. The cyclic siloxane compound according to claim 1 , wherein the phosphorescent compound is an iridium complex.

6. A process of producing a cyclic siloxane compound represented by Formula (1) below:

wherein, in Formula (1), R 1 and R 2 are each independently a luminescent monovalent group, a charge-transporting monovalent group, or another substituent; at least one of R 1 and R 2 is the charge-transporting monovalent group and at least one of R 1 and R 2 is the luminescent monovalent group; and n is an integer of 2 to 100, the said process comprising:

cyclocondensing monomers represented by Formula (10) below:

wherein, in Formula (10), R 1 and R 2 are each independently the same as R 1 and R 2 in Formula (1); and X 1 and X 2 are each independently a hydroxyl group, an alkoxy group, or a halogen atom; wherein the luminescent monovalent group is obtained by substituting a hydrogen atom of a phosphorescent compound represented by any one of Formulae (E-1) to (E-49) below with a linking group X A ; X A is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and the luminescent monovalent group is linked to a Si atom in Formula (1) via the linking group X A ;

the charge-transporting monovalent group is obtained by substituting a hydrogen atom of a charge-transporting compound represented by any one of Formulae (E-50) to (E-67) below with a linking group X B ; and is linked to a Si atom in Formula (1) via the linking group X B ; X B is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and

the another substituent group is selected from the group consisting of aryl groups having 6 to 60 carbon atoms, monovalent heterocyclic groups, alkyl groups having 1 to 20 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms and aryloxyalkyl groups having 7 to 60 carbon atoms:

7. A process of producing a cyclic siloxane compound represented by Formula (1) below:

wherein, in Formula (1), R 1 and R 2 are each independently a luminescent monovalent group, a charge-transporting monovalent group, or another substituent; at least one of R 1 and R 2 is the charge-transporting monovalent group and at least one of R 1 and R 2 is the luminescent monovalent group; and n is an integer of 2 to 100, the said process comprising:

reacting a cyclic siloxane compound represented by Formula (20) below:

wherein, in Formula (20), R 3 is a hydrogen atom or the another substituent, and n is an integer of 2 to 100, with a charge-transporting compound having a vinyl group and capable of inducing the charge-transporting monovalent group and/or a luminescent compound having a vinyl group and capable of inducing the luminescent monovalent group; wherein the luminescent monovalent group is obtained by substituting a hydrogen atom of a phosphorescent compound represented by any one of Formulae (E-1) to (E-49) below with a linking group X A ; X A is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and the luminescent monovalent group is linked to a Si atom in Formula (1) via the linking group X A ;

the charge-transporting monovalent group is obtained by substituting a hydrogen atom of a charge-transporting compound represented by any one of Formulae (E-50) to (E-67 below with a linking group X B , and is linked to a Si atom in Formula (1) via the linking group X B ; X B is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and

the another substituent group is selected from the group consisting of aryl groups having 6 to 60 carbon atoms, monovalent heterocyclic groups, alkyl groups having 1 to 20 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms and aryloxyalkyl groups having 7 to 60 carbon atoms:

8. A process of producing a cyclic siloxane compound represented by Formula (1) below:

wherein, in Formula (1), R 1 and R 2 are each independently a luminescent monovalent group, a charge-transporting monovalent group, or another substituent; at least one of R 1 and R 2 is the charge-transporting monovalent group and at least one of R 1 and R 2 is the luminescent monovalent group; and n is an integer of 2 to 100, the said process comprising:

reacting a cyclic siloxane compound represented by Formula (30) below:

wherein, in Formula (30), R 4 and R 5 are each independently a substituent having a reactive group or the another substituent; at least one of R 4 and R 5 is the substituent having a reactive group; and n is an integer of 2 to 100, with a charge-transporting compound capable of inducing the charge-transporting monovalent group and/or a luminescent compound capable of inducing the luminescent monovalent group; wherein the luminescent monovalent group is obtained by substituting a hydrogen atom of a phosphorescent compound represented by any one of Formulae (E-1) to (E-49) below with a linking group X A ; X A is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and the luminescent monovalent group is linked to a Si atom in Formula (1) via the linking group X A ;

the charge-transporting monovalent group is obtained by substituting a hydrogen atom of a charge-transporting compound represented by any one of Formulae (E-50) to (E-67) below with a linking group X B , and is linked to a Si atom in Formula (1) via the linking group X B ; X B is a single bond or a group represented by —(CH 2 ) n —, wherein n is an integer of 1 to 20; and

the another substituent group is selected from the group consisting of aryl groups having 6 to 60 carbon atoms, monovalent heterocyclic groups, alkyl groups having 1 to 20 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms and aryloxyalkyl groups having 7 to 60 carbon atoms:

9. An organic electroluminescence device comprising a substrate, a pair of electrodes disposed on the substrate and, between the pair of electrodes, one or more organic layers having a luminescent layer, wherein the luminescent layer comprises the cyclic siloxane compound of claim 1 .

10. An image display apparatus comprising the organic electroluminescence device of claim 9 .

11. An area light source comprising the organic electroluminescence device of claim 9 .

12. An organic electroluminescence device comprising a substrate, a pair of electrodes disposed on the substrate and, between the pair of electrodes, one or more organic layers having a luminescent layer, wherein the luminescent layer comprises the cyclic siloxane compound of claim 1 and an electron-transporting material, and said electron-transporting material being selected from the group consisting of a low molecular weight compound selected from the group consisting of an oxadiazole derivative, a triazole derivative, an imidazole derivative, a triazine derivative and a triarylborane derivative; a high molecular weight compound obtained by introducing polymerizable substituents into the low molecular weight compound followed by polymerizing; and a cyclic siloxane compound represented by Formula (1′) below:

wherein, in Formula (1′), R 1 and R 2 are each independently a luminescent monovalent group, a charge-transporting monovalent group, or another substituent group; at least one of R 1 and R 2 is the charge-transporting monovalent group; and n is an integer of 2 to 100, wherein charge-transporting monovalent group is obtained by substituting a hydrogen atom of a charge-transporting compound represented by any one of Formulae (E-59) to (E-67) below with a linking group X B , and is linked to a Si atom in Formula (1′) via the linking group X B :

13. The cyclic siloxane compound according to claim 1 , wherein n is an integer of 10 to 100.

14. The cyclic siloxane compound according to claim 1 , wherein n is an integer of 30 to 100.