Polymer compound and light emitting device using the same
A polymer compound comprising a constitutional unit represented by the following formula (1) and a constitutional unit represented by the following formula (X) and/or a constitutional unit represented by the following formula (Y), wherein the content of the hydroxyl groups contained in the polymer compound is less than 0.02 mol %: Ar 1 (1) [wherein, Ar 1 represents an arylene group and this group optionally has a substituent.] [wherein, a X1 and a X2 each independently represent an integer of 0 or more. Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group and these groups each optionally have a substituent. Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, and these groups each optionally have a substituent. When there are a plurality of Ar X2 and a plurality of Ar X4 , each of them may be the same or different. R X1 , R X2 and R X3 each independently represent an alkyl group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent. When there are a plurality of R X2 and a plurality of R X3 , each of them may be the same or different.] Ar Y1 (Y) [wherein, Ar Y1 represents an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, and these groups each optionally have a substituent.].
1. A method for producing a polymer compound comprising a constitutional unit represented by the following formula (1) and a constitutional unit represented by the following formula (X) and/or a constitutional unit represented by the following formula (Y), wherein the constitutional unit represented by the formula (1) is a constitutional unit represented by the following formula (1-1) or (1-2), the constitutional unit represented by the formula (X) is a constitutional unit represented by the following formula (X-1), (X-2), (X-3), (X-4), (X-5), (X-6), or (X-7), and the constitutional unit represented by the formula (Y) is a constitutional unit represented by the following formula (Y-3), (Y-4), (Y-5), (Y-6), or (Y-7),
wherein the content of the hydroxyl groups contained in the polymer compound is less than 0.02 mol % and the content of the phosphorus atoms contained in the polymer compound is less than 50 ppm:
Ar 1 (1)
wherein Ar 1 represents an arylene group and this group optionally has a substituent,
wherein R 1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and the R 1 s may be the same or different and adjacent R 1 s may be combined together to form a ring together with the carbon atoms to which they are attached,
wherein
R 1 represents the same meaning as described above, and
X 1 represents a group represented by —C(R 2 ) 2 —, —C(R 2 )═C(R 2 )— or C(R 2 ) 2 —C(R 2 ) 2 —, and R 2 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and the R 2 s may be the same or different and the R 2 s may be combined together to form a ring together with the carbon atoms to which they are attached,
wherein
a X1 and a X2 each independently represent an integer of 0 or more,
Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group and these groups each optionally have a substituent,
Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, and these groups each optionally have a substituent, and when there are a plurality of Ar X2 and a plurality of Ar X4 , each of them may be the same or different, and
R X1 , R X2 and R X3 each independently represent an alkyl group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and when there are a plurality of R X2 and a plurality of R X3 , each of them may be the same or different,
wherein R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a fluorine atom, a monovalent heterocyclic group or a cyano group and these groups each optionally have a substituent, and the R X4 s may be the same or different, and the R X5 s may be the same or different and adjacent R X5 s may be combined together to form a ring together with the carbon atoms to which they are attached,
Ar Y1 (Y)
wherein Ar Y1 represents an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, and these groups each optionally have a substituent,
wherein
R Y1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and the R Y1 s may be the same or different and adjacent R Y1 s may be combined together to form a ring together with the carbon atoms to which they are attached, and
R Y3 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent,
wherein
R Y1 represents the same meaning as described above, and
R Y4 represents an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent,
the method comprising a step of Suzuki polymerizing a compound represented by the following formula (M-1) and a compound represented by the following formula (M-X) and/or a compound represented by the following formula (M-Y), wherein the compound represented by the formula (M-Y) differs from the compound represented by the formula (M-1) in the presence of a dichlorobis(dicyclopentyl(o-methoxyphenyl)phosphinepalladium catalyst, a base, and a solvent, under a condition of an oxygen concentration of less than 0.2%:
wherein
Ar 1 , a X1 , a X2 , Ar X1 , Ar X3 , Ar X2 , Ar X4 , R X1 , R X2 , R X3 and Ar Y1 represent the same meanings as described above, and
Z C1 and Z C2 each independently represent a group selected from Group B substituents, and Z C3 , Z C4 , Z C5 and Z C6 each independently represent a group selected from Group A substituents,
Group A substituents comprise:
a chlorine atom, a bromine atom, and an iodine atom
Group B substituents comprise:
a group represented by —B(OR C2 ) 2 , wherein R C2 represents a hydrogen atom, an alkyl group or an aryl group and these groups each optionally have a substituent, and the R C2 s may be the same or different and may be combined together to form a ring together with the oxygen atoms to which they are attached.
2. The method according to claim 1 , wherein the solvent is a mixed solvent comprising an organic solvent and water.
3. The method according to claim 2 , wherein the organic solvent is toluene, xylene or mesitylene.
4. The method according to claim 3 , wherein the organic solvent is toluene.
5. The method according to claim 1 , wherein the polymer compound comprises a constitutional unit represented by the formula (1) and a constitutional unit represented by the following formula (Y-3), (Y-4), (Y-5), (Y-6) or (Y-7):