POLYMER COMPOUND AND LIGHT EMITTING DEVICE USING THE SAME

Abstract

A polymer compound having an excellent crosslinking ability is provided. The polymer compound has at least one terminal constitutional unit represented by the formula (1) and a constitutional unit represented by the formula (2):

##STR00001##

In the constitutional unit represented by formula (1), mT represents an integer of 0 to 5, nT represents an integer of 1 to 4, cT represents an integer of 0 to 1, Q.sup.T represents a crosslinkable group, K.sup.T represents an alkylene group or the like and Ar.sup.T represents an aromatic hydrocarbon group or the like. In the constitutional unit represented by formula (2), mA represents an integer of 0 to 5, n represents an integer of 1 to 4, Ar.sup.1 represents an aromatic hydrocarbon group or the like, K.sup.A represents an alkylene group or the like and Q.sup.1 represents a crosslinkable group.

Claims

1. A polymer compound comprising: at least one terminal constitutional unit represented by the following formula (1) and at least one type of constitutional unit selected from the group consisting of constitutional units represented by the following formula (2) and constitutional units represented by the following formula (2′): ##STR00180## wherein mT represents an integer of 0 to 5, nT represents an integer of 1 to 4, and cT represents 0 or 1, and when there are a plurality of mT, they may be the same or different, and nT is 1 when cT is 0, Q.sup.T represents a crosslinkable group represented by the following formula (XL-1), (XL-7), (XL-16) or (XL-17), and when there are a plurality of Q.sup.T, they may be the same or different, K.sup.T represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′—, an oxygen atom or a sulfur atom, the foregoing groups each optionally having a substituent, wherein R′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of K.sup.T, they may be the same or different, and Ar.sup.T represents an aromatic hydrocarbon group or a heterocyclic group, the foregoing groups each optionally having a substituent; ##STR00181## wherein mA represents an integer of 0 to 5, and n represents 1 or 2, and when there are a plurality of mA, they may be the same or different, Ar.sup.1 represents an aromatic hydrocarbon group or a heterocyclic group, the foregoing groups each optionally having a substituent, K.sup.A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR″—, an oxygen atom or a sulfur atom, the foregoing groups each optionally having a substituent, wherein R″ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of K.sup.A, they may be the same or different, and Q.sup.1 represents a crosslinkable group selected from Group A of crosslinkable groups, and when there are a plurality of Q.sup.1, they may be the same or different; ##STR00182## wherein mB represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1, and when there are a plurality of mB, they may be the same or different, Ar.sup.3 represents an aromatic hydrocarbon group, a heterocyclic group or a group in which at least one type of aromatic hydrocarbon ring and at least one type of heterocyclic ring are bonded directly to each other, the foregoing groups each optionally having a substituent, Ar.sup.2 and Ar.sup.4 each independently represent an arylene group or a divalent heterocyclic group, the foregoing groups each optionally having a substituent, each of groups Ar2, Ar3 and Ar4 is optionally bonded directly or via an oxygen atom or a sulfur atom to a group that is attached to the nitrogen atom to which that group is attached but that is different from that group itself, thereby forming a ring, K.sup.B represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′″—, an oxygen atom or a sulfur atom, the foregoing groups each optionally having a substituent, wherein R′″ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of K.sup.B, they may be the same or different, and Q.sup.2 represents a crosslinkable group selected from Group A of crosslinkable groups, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of Q.sup.2, they may be the same or different, provided that at least one Q.sup.2 is a crosslinkable group selected from Group A of crosslinkable groups, wherein Group A is a crosslinkable group selected from the group consisting of: ##STR00183## ##STR00184## wherein R.sup.XL represents a methylene group, an oxygen atom or a sulfur atom, and n.sup.XL represents an integer of 0 to 5, and when there are a plurality of R.sup.XL, they may be the same or different, and when there are a plurality of n.sup.XL, they may be the same or different, and * represents a binding site, the foregoing crosslinkable groups each optionally having a substituent.

2. (canceled)

3. The polymer compound according to claim 1, wherein Q.sup.1 is a crosslinkable group represented by the formula (XL-1), (XL-7), (XL-16) or (XL-17).

4. The polymer compound according to claim 1, wherein Q.sup.2 is a crosslinkable group represented by the formula (XL-1), (XL-7), (XL-16) or (XL-17).

5. The polymer compound according to claim 1, wherein cT is 0.

6. The polymer compound according to claim 1, wherein cT is 1, and Ar.sup.T is a group obtained by removing from a benzene ring optionally having a substituent, a fluorene ring optionally having a substituent, a naphthalene ring optionally having a substituent, a phenanthrene ring optionally having a substituent or a dihydrophenanthrene ring optionally having a substituent (nT+1) hydrogen atoms attached directly to carbon atoms constituting the ring.

7. The polymer compound according to claim 1, further comprising a constitutional unit represented by the following formula (X): ##STR00185## wherein a.sup.1 and a.sup.2 each independently represent an integer of 0 or more, Ar.sup.X1 and Ar.sup.X3 each independently represent an arylene group or a divalent heterocyclic group, the foregoing groups each optionally having a substituent, Ar.sup.X2 and Ar.sup.X4 each independently represent an arylene group, a divalent heterocyclic group or a divalent group in which at least one type of arylene group and at least one type of divalent heterocyclic group are bonded directly to each other, the foregoing groups each optionally having a substituent, and when there are a plurality of Ar.sup.X2 or Ar.sup.X4, they may be the same or different at each occurrence, and R.sup.X1, R.sup.X2 and R.sup.X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of R.sup.X2 or R.sup.X3, they may be the same or different at each occurrence.

8. The polymer compound according to claim 1, further comprising a constitutional unit represented by the following formula (Y):
Ar.sup.Y1  (Y) wherein Ar.sup.Y1 represents an arylene group, a divalent heterocyclic group or a divalent group in which at least one type of arylene group and at least one type of divalent heterocyclic group are bonded directly to each other, the foregoing groups each optionally having a substituent.

9. The polymer compound according to claim 8, wherein the constitutional unit represented by the formula (Y) is a constitutional unit represented by the following formula (Y-1) or a constitutional unit represented by the following formula (Y-2): ##STR00186## wherein R.sup.Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of R.sup.Y1 may be the same or different, and adjacent groups R.sup.Y1 may be combined together to form a ring together with the carbon atoms to which they are attached: ##STR00187## wherein R.sup.Y1 is as defined above, and X.sup.Y1 represents a group represented by —C(R.sup.Y2).sub.2—, —C(R.sup.Y2)═C(R.sup.Y2)— or —C(R.sup.Y2).sub.2—C(R.sup.Y2).sub.2—, wherein R.sup.Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of R.sup.Y2 may be the same or different, and groups R.sup.Y2 may be combined together to form a ring together with the carbon atoms to which they are attached.

10. The polymer compound according to claim 1, wherein the terminal constitutional unit represented by the formula (1) is contained in an amount of 0.1 mol % to 20 mol % with respect to the total amount of constitutional units contained in the polymer compound.

11. A method for producing the polymer compound according to claim 1, comprising a step of condensation-polymerizing at least one type of compound selected from the group consisting of a compound represented by the following formula (2M) and a compound represented by the following formula (2′M), and a step of end capping with a compound represented by the following formula (1M), ##STR00188## wherein mA, n, Ar.sup.1, K.sup.A and Q.sup.1 are as defined above, and Z.sup.1 and Z.sup.2 each independently represent a group selected from Group A of substituents or a group selected from Group B of substituents, ##STR00189## wherein mB, m, c, Ar.sup.2, Ar.sup.3, Ar.sup.4, K.sup.B and Q.sup.2 are as defined above, and Z.sup.3 and Z.sup.4 each independently represent a group selected from Group A of substituents or a group selected from Group B of substituents, ##STR00190## wherein mT, nT, cT, Q.sup.T, K.sup.T and Ar.sup.T are as defined above, and Z.sup.T represents a group selected from Group A of substituents or a group selected from Group B of substituents: Group A is a substituent selected from the group consisting of a chlorine atom, a bromine atom, an iodine atom, and a group represented by —O—S(═O).sub.2R.sup.C1, wherein R.sup.C1 represents an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, Group B is a substituent selected from the group consisting of a group represented by —B(OR.sup.C2).sub.2, wherein R.sup.C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and the plurality of R.sup.C2 may be the same or different and may be combined together to form a cyclic structure together with the oxygen atoms to which they are attached; a group represented by —BF.sub.3 Q′, wherein Q′ represents Li, Na, K, Rb or Cs; a group represented by —MgY′, wherein Y′ represents a chlorine atom, a bromine atom or an iodine atom; a group represented by —ZnY″, wherein Y″ represents a chlorine atom, a bromine atom or an iodine atom; and a group represented by —Sn(R.sup.C3).sub.3, wherein R.sup.C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and the plurality of R.sup.C3 may be the same or different and may be combined together to form a cyclic structure together with the tin atom to which they are attached.

12. The polymer compound according to claim 1 produced by a production method comprising a step of condensation-polymerizing at least one type of compound selected from the group consisting of a compound represented by the following formula (2M) and a compound represented by the following formula (2′M), and a step of end capping with a compound represented by the following formula (1M), ##STR00191## wherein mA, n, Ar.sup.1, K.sup.A and Q.sup.1 are as defined above, and Z.sup.1 and Z.sup.2 each independently represent a group selected from Group A of substituents or a group selected from Group B of substituents, ##STR00192## wherein mB, m, c, Ar.sup.2, Ar.sup.3, Ar.sup.4, K.sup.B and Q.sup.2 are as defined above, and Z.sup.3 and Z.sup.4 each independently represent a group selected from Group A of substituents or a group selected from Group B of substituents, ##STR00193## wherein mT, nT, cT, Q.sup.T, K.sup.T and Ar.sup.T are as defined above, and Z.sup.T represents a group selected from Group A of substituents or a group selected from Group B of substituents: Group A is a substituent selected from the group consisting of a chlorine atom, a bromine atom, an iodine atom, and a group represented by —O—S(═O).sub.2 R.sup.C1, wherein R.sup.C1 represents an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, Group B is a substituent selected from the group consisting of a group represented by —B(OR.sup.C2).sub.2, wherein R.sup.C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and the plurality of R.sup.C2 may be the same or different and may be combined together to form a cyclic structure together with the oxygen atoms to which they are attached; a group represented by —BF.sub.3 Q′, wherein Q′ represents Li, Na, K, Rb or Cs; a group represented by —MgY′, wherein Y′ represents a chlorine atom, a bromine atom or an iodine atom; a group represented by —ZnY″, wherein Y″ represents a chlorine atom, a bromine atom or an iodine atom; and a group represented by —Sn(R.sup.C3).sub.3, wherein R.sup.C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and the plurality of R.sup.C3 may be the same or different and may be combined together to form a cyclic structure together with the tin atom to which they are attached.

13. A composition comprising: the polymer compound according to claim 1, and at least one type of material selected from the group consisting of a hole transporting material, a hole injection material, an electron transporting material, an electron injection material, a light emitting material, an antioxidant and a solvent.

14. A light emitting device produced by using the polymer compound according to claim 1.

Description

EXAMPLES

[0345] The present invention will be illustrated further in detail by examples below, but the present invention is not limited to these examples.

[0346] In the present examples, the polystyrene-equivalent number average molecular weight (Mn) and the polystyrene-equivalent weight average molecular weight (Mw) of a polymer compound were measured by size exclusion chromatography (SEC) (manufactured by Shimadzu Corp., trade name: LC-10Avp). SEC measurement conditions are as described below.

[Measurement Condition]

[0347] The polymer compound to be measured was dissolved in tetrahydrofuranat a concentration of about 0.05 wt %, and 10 μL of the solution was injected into SEC. As the mobile phase of SEC, tetrahydrofuran was used and allowed to flow at a flow rate of 1.0 mL/min. As the column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. As the detector, UV-VIS detector (manufactured by Tosoh., trade name: UV-8320GPC) was used.

[0348] LC-MS was measured by the following method.

[0349] A measurement sample was dissolved in chloroform or tetrahydrofuran so as to give a concentration of about 2 mg/mL, and about 1 μL of the solution was injected into LC-MS (manufactured by Agilent Technologies, trade name: 1100LCMSD). As the mobile phase of LC-MS, acetonitrile and tetrahydrofuran were used while changing the ratio thereof and allowed to flow at a flow rate of 0.2 mL/min. As the column, L-column 2 ODS (3 μm) (manufactured by Chemicals Evaluation and Research Institute, internal diameter: 2.1 mm, length: 100 mm, particle size: 3 μm) was used.

[0350] TLC-MS was measured by the following method.

[0351] A measurement sample was dissolved at an arbitrary concentration in any solvent of toluene, tetrahydrofuran or chloroform, the solution was applied on a TLC plate for DART (manufactured by Techno Applications Inc., trade name: YSK5-100), and TLC-IS was measured using The AccuTOF TLC (trade name: JMS-T100TD, manufactured by JEOL Lt.). The temperature of a helium gas in measurement was controlled in the range of 200 to 400° C.

[0352] NMR was measured by the following method.

[0353] Five to ten milligrams (5 to 10 mg) of a measurement sample was dissolved in about 0.5 mL of deuterated chloroform (CDCl.sub.3), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N,N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol or deuterated methylene chloride, and NMR was measured using an NMR apparatus (manufactured by Agilent Technologies, Inc., trade name: INOVA300 or MERCURY 400VX).

[0354] As the index of the purity of a compound, a value of the high performance liquid chromatography (HPLC) area percentage was used. This value is a value in high performance liquid chromatography (HPLC, manufactured by Shimadzu Corp., trade name: LC-20A) at 254 nm, unless otherwise state. In this operation, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to give a concentration of 0.01 to 0.2% by weight, and depending on the concentration, 1 to 10 μL of the solution was injected into HPLC. As the mobile phase of HPLC, acetonitrile and tetrahydrofuran were used while varying the ratio of acetonitrile/tetrahydrofuran from 100/0 to 0/100 (voluminal ratio) and allowed to flow at a flow rate of 1.0 mL/min. As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical industry Co., Ltd.) or an CDS column having an equivalent performance was used. As the detector, a photo diode array detector (manufactured by Shimadzu Corp., trade name: SPD-M20A) was used.

<Synthesis Example 1> Synthesis of Compound MM1

[0355] ##STR00146##

[0356] A nitrogen gas atmosphere was prepared in a reaction vessel, then, 4-bromobenzocyclobutene (1000 g), bis(pinacolato)diboron (1404 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex (40 g), potassium acetate (1628 g), 1,1′-bis(diphenylphosphino)ferrocene (26.6 g) and 1,4-dioxane (10.9 L) were added, and the mixture was stirred for 5 hours while heating under reflux. Thereafter, the mixture was cooled down to room temperature, filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant residue was dissolved in hexane (5 L), activated carbon (1000 g) was added, then, the mixture was stirred. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain a crude product. An operation of recrystallizing the resultant crude product using pentane was conducted repeatedly, to obtain a compound MM1 (754 g) as a white solid.

[0357] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.33 (12H, s), 3.18 (4H, s), 7.06 (1H, d), 7.49 (1H, s), 7.68 (1H, d).

<Synthesis Example 2> Synthesis of Compound MM2-St1

[0358] ##STR00147##

[0359] A nitrogen gas atmosphere was prepared in a reaction vessel, then, 4-bromoanisole (200 g) and tetrahydrofuran (3.5 L) were added, and the mixture was cooled down to −78° C. Thereafter, to this was added a sec-butyllithium cyclohexane solution (1.4 mol/L, 1.67 L), and the mixture was stirred at −78° C. for 4 hours. Thereafter, to this was added a tetrahydrofuran solution prepared by dissolving 4-bromo-1-chlorobutane (208 g) in tetrahydrofuran (2.0 L), and the mixture was heated up to room temperature, then, stirred at room temperature for 16 hours. Thereafter, to this were added ammonium chloride water and ethyl acetate, and an aqueous layer and an organic layer were separated. To the resultant organic layer was added sodium sulfate, and the mixture was filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a crude product. The resultant crude product was purified by a silica gel column using a mixed solvent of ethyl acetate and hexane as a developing solvent, to obtain 166 g of a compound MM2-st1 as yellow oil.

[0360] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.69-1.86 (m, 4H), 2.59 (t, 2H), 3.55 (t, 2H), 3.80 (s, 3H), 6.84 (d, 2H), 7.11 (d, 2H).

<Synthesis Example 3> Synthesis of Compound MM2-St2

[0361] ##STR00148##

[0362] A nitrogen gas atmosphere was prepared in a reaction vessel, then, 1,2-dibromoethane (2 mL) and tetrahydrofuran (1.5 L) were added, the, magnesium (40.6 g) was added, and the mixture was heated up to 75° C. Thereafter, to this was added the compound MM2-st1 (166 g), and the mixture was heated under reflux for 4 hours. The resultant reaction mixture was added to a tetrahydrofuran solution prepared by dissolving 4-bromobenzocyclobutane (102 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex (22.7 g) in tetrahydrofuran (1.0 L), and the mixture was stirred at 75° C. for 16 hours. Thereafter, to this were added dilute hydrochloric acid water and ethyl acetate, and an aqueous layer and an organic layer were separated. To the resultant organic layer was added sodium sulfate, and the mixture was filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a crude product. The resultant crude product was purified by a silica gel column using a mixed solvent of ethyl acetate and hexane as a developing solvent, to obtain 85 g of a compound MM2-st2 as yellow oil. This operation was repeated, to obtain a necessary amount of the compound MM2-st2.

[0363] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.62-1.66 (m, 4H), 2.57-2.62 (m, 4H), 3.15 (s, 4H), 3.80 (s, 3H), 6.83 (d, 2H), 6.89 (s, 1H), 6.96 (d, 1H), 7.0 (d, 1H), 7.10 (d, 2H).

<Synthesis Example 4> Synthesis of Compound MM2-St3

[0364] ##STR00149##

[0365] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound MM2-st2 (90 g) and dichloromethane (1.0 L) were added, and the mixture was cooled down to −78° C. Thereafter, to this was added a tribromoborane dichloromethane solution (1 mol/L, 304 mL), and the mixture was stirred at −78° C. for 2 hours. The resultant reaction mixture was heated up to room temperature, then, stirred at room temperature for 18 hours. The resultant reaction mixture was washed with water, then, dichloromethane was added, and an aqueous layer and an organic layer were separated. To the resultant organic layer was added sodium sulfate, and the mixture was filtrated. The resultant filtrate was concentrated, to obtain a crude product. The resultant crude product was purified by a silica gel column using a mixed solvent of tert-butyl methyl ether and hexane as a developing solvent, to obtain 45 g of a compound MM2-st3 as a white solid.

[0366] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.60-1.65 (m, 4H), 2.55-2.62 (m, 4H), 3.15 (s, 4H), 4.68 (brs, 1H), 6.75 (d, 2H), 6.89 (s, 1H), 6.96 (d, 1H), 7.01 (d, 1H), 7.04 (d, 2H).

<Synthesis Example 5> Synthesis of Compound MM2-st4

[0367] ##STR00150##

[0368] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound MM2-st3 (45 g), pyridine (31.7 mL) and dichloromethane (450 mL) were added, and the mixture was cooled down to 0° C. Thereafter, to this was added trifluoromethanesulfonic anhydride (43.8 mL), and the mixture was stirred at 0° C. for 1 hour. The resultant reaction mixture was heated up to room temperature, then, stirred at room temperature for 1 hour. Thereafter, to this were added water and dichloromethane, and an aqueous layer and an organic layer were separated. To the resultant organic layer was added sodium sulfate, and the mixture was filtrated. The resultant filtrate was concentrated, to obtain a crude product. The resultant crude product was purified by a silica gel column using hexane as a developing solvent, to obtain 50 g of a compound MM2-st4 as pale yellow oil.

[0369] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.64-1.67 (m, 4H), 2.59-2.68 (m, 4H), 3.15 (s, 4H), 6.89 (s, 1H), 6.97 (d, 1H), 7.0 (d, 1H), 7.17 (d, 2H), 7.23 (d, 2H).

<Synthesis Example 6> Synthesis of Compound MM2

[0370] ##STR00151##

[0371] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound MM2-st4 (50 g), bis(pinacolato)diboron (99.0 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex (2.65 g), potassium acetate (38.3 g) and 1,4-dioxane (600 mL) were added, and the mixture was heated up to 110° C., and stirred at 110° C. for 16 hours. The resultant reaction mixture was cooled down to room temperature, then, filtrated, and the resultant filtrate was concentrated under reduced pressure. To the resultant residue were added ethyl acetate and water, and an aqueous layer and an organic layer were separated. To the resultant organic layer was added sodium sulfate, and the mixture was filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a crude product. The resultant crude product was purified by a silica gel column repeatedly, to obtain 33 g of a compound MM2 as a white solid.

[0372] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.36 (s, 12H), 1.63-1.67 (m, 4H), 2.59-2.68 (m, 4H), 3.15 (s, 4H), 6.89 (s, 1H), 6.97 (d, 1H), 7.0 (d, 1H), 7.20 (d, 2H), 7.23 (d, 2H).

<Synthesis Example 7> Synthesis of Compound MM3-st1

[0373] ##STR00152##

[0374] A nitrogen gas atmosphere was prepared in a reaction vessel, then, 2-bromofluorene (4.92 g), 5-bromo-1-pentene (8.94 g), tetrabutylammonium bromide (324 mg) and a potassium hydroxide aqueous solution (50% by weight, 17 mL) were added, and the mixture was heated up to 80° C., and stirred at 80° C. for 4 hours. The resultant reaction mixture was cooled down to room temperature, water and heptane were added to this, and an aqueous layer and an organic layer were separated. To the resultant organic layer was added magnesium sulfate, and the mixture was filtrated. The resultant filtrate was concentrated under reduced pressure, then, to the resultant residue were added heptane and activated carbon (2.20 g), and the mixture was stirred for 30 minutes. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain 6.78 g of a compound MM3-st1 as pale yellow oil.

[0375] LC-MS (APPI, positive): M.sup.+ 380

<Synthesis Example 8> Synthesis of Compound MM3

[0376] ##STR00153##

[0377] An argon gas atmosphere was prepared in a reaction vessel, then, the compound MM3-st1 (6.00 g) and tetrahydrofuran (90 mL) were added, and the mixture was cooled down to −78° C. Thereafter, to this was added a solution (1.07 mol/L, 29.4 mL) prepared by dissolving sec-butyllithium in cyclohexane, and the mixture was stirred at −78° C. for 1 hour. Thereafter, to this was added 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (6.59 g), and the mixture was heated up to room temperature, then, water and heptane were added, and an aqueous layer and an organic layer were separated. The resultant organic layer was washed with water, then, magnesium sulfate was added, and the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain a crude product. The resultant crude product was purified by a silica gel column using a mixed solvent of hexane and toluene as a developing solvent, then, concentrated under reduced pressure. To the resultant residue were added heptane and activated carbon (1.40 g), and the mixture was stirred for 30 minutes. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain 3.36 g of a compound MM3 as colorless oil.

[0378] LC-MS (APPI, positive): M.sup.+ 428

[0379] .sup.1H-NMR (CDCl.sub.3, 300 Hz) δ (ppm): 0.68 (s, 4H), 0.97 (s, 12H), 1.79 (m, 4H), 2.00 (m, 4H), 4.75-4.87 (m, 4H), 5.55 (m, 2H), 7.28-7.38 (m, 3H), 7.67-7.76 (m, 3H), 7.80 (dd, 1H).

<Synthesis Example 9> Synthesis of Compound MM4-st1

[0380] ##STR00154##

[0381] A nitrogen gas atmosphere was prepared in a reaction vessel, then, magnesium (44.1 g), diethyl ether (18 mL) and several fragments of iodine were added, then, a solution prepared by dissolving neopentyl bromide (206 mL) in diethyl ether (518 mL) was added, and the mixture was stirred under reflux for 1 hour. The resultant reaction mixture was added to a solution prepared by dissolving a compound MM4-st0 (179 g) synthesized according to a synthesis method described in JP-A No. 2014-133740 in diethyl ether (1800 mL), then, the mixture was stirred overnight at room temperature. Thereafter, to this was added dilute hydrochloric acid water (540 mL), then, the mixture was washed with water. To the resultant organic layer was added magnesium sulfate, and the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant solid was dissolved in toluene, then, the solution was filtrated through silica gel, and the resultant filtrate was concentrated under reduced pressure, to obtain 225 g of a crude product. The crude product (250 g) obtained by repeating this operation was recrystallized from hexane, to obtain 151 g of a compound MM4-st1 as a white solid.

[0382] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 1.10 (9H, s), 1.81 (1H, d), 1.94 (1H, d), 2.09 (1H, s), 3.16 (1H, d), 3.49 (1H, d), 7.07 (1H, d), 7.30 (1H, s), 7.37 (1H, d).

<Synthesis Example 10> Synthesis of Compound MM4-st2

[0383] ##STR00155##

[0384] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound MM4-st1 (150 g), hexane (300 mL) and triethylsilane (96.5 mL) were added, and the mixture was cooled down to 0° C. Thereafter, into this was dropped trifluoroacetic acid (220 mL) over a period of 0.5 hours. The resultant reaction mixture was heated up to 30° C., and stirred at 30° C. for 1 hour, then, stirred overnight at room temperature. To the resultant reaction mixture were added hexane and water, and an aqueous layer and an organic layer were separated. The resultant organic layer was washed with 10% by weight sodium acetate water and water. To the resultant organic layer was added magnesium sulfate, and the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant yellow oil was dissolved in hexane, then, the solution was filtrated through silica gel, and the resultant filtrate was concentrated under reduced pressure, to obtain 166 g of a crude product of a compound MM4-st2 as colorless oil.

[0385] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the colorless oil (166 g) obtained above and tetrahydrofuran (1500 mL) were added, then, a borane.THF complex (0.28 mol/L tetrahydrofuran solution, 237 mL) was dropped, then, the mixture was stirred at 50° C. for 0.5 hours. The resultant reaction mixture was cooled down to room temperature, then, hexane and water were added, and an aqueous layer and an organic layer were separated. The resultant organic layer was washed with water, then, magnesium sulfate was added, and the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant crude product was purified by a silica gel column (a developing solvent: hexane), to obtain 136 g of a compound MM4-st2 as colorless oil.

[0386] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 0.99 (9H, s), 1.54 (1H, dd), 1.74 (1H, dd), 2.78 (1H, dd), 3.36 (1H, dd), 3.47 (1H, m), 6.92 (1H, d), 7.18 (1H, s), 7.31 (1H, d).

<Synthesis Example 11> Synthesis of Compound MM4

[0387] ##STR00156##

[0388] An argon gas atmosphere was prepared in a reaction vessel, then, the compound MM4-st2 (1.06 g), bis(pinacolato)diboron (1.26 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex (158 mg), potassium acetate (2.39 g) and 1,2-dimethoxyethane (10 mL) were added, and the mixture was heated up to 80° C., and stirred at 80° C. for 5 hours. The resultant reaction mixture was cooled down to room temperature, then, heptane and water were added, and an aqueous layer and an organic layer were separated. The resultant organic layer was washed with water, then, magnesium sulfate was added, and the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant residue was dissolved in toluene, then, the solution was filtrated through silica gel, and the resultant filtrate was concentrated under reduced pressure. The residue (1.37 g) obtained by repeating this operation was dissolved in heptane (14 mL), then, activated carbon (359 mg) was added, and the mixture was stirred. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain a crude product. The resultant crude product was recrystallized from acetonitrile, to obtain a compound MM4 (730 mg) as a white solid.

[0389] LC-MS (ESI, positive): [M+K].sup.+ 339

[0390] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 0.99 (9H, s), 1.33 (12H, s), 1.55 (1H, dd), 1.78 (1H, dd), 2.78 (1H, dd), 3.37 (1H, dd), 3.54 (1H, m), 7.07 (1H, d), 7.49 (1H, s), 7.67 (1H, d).

<Synthesis Example 12> Synthesis of Compounds MM10 to MM20

[0391] A compound MM10 was synthesized according to a synthesis method described in international Publication WO2002/092723.

[0392] A compound MM11 was synthesized according to a synthesis method described in JP-A No. 2011-174062.

[0393] A compound MM12 was synthesized according to a synthesis method described in international Publication WO2005/049546.

[0394] A compound MM13 was synthesized according to a synthesis method described in JP-A No. 2010-215886.

[0395] A compound MM14 was synthesized according to a synthesis method described in international Publication WO2002/045184.

[0396] A compound MM15 was synthesized according to a synthesis method described in JP-A No. 2008-106241.

[0397] A compound MM16 was synthesized according to the following synthesis method.

[0398] A compound MM17 was synthesized according to a synthesis method described in international Publication WO2013/146806.

[0399] A compound MM18 was synthesized according to the following synthesis method.

[0400] A compound MM19 was synthesized according to a synthesis method described in International Publication WO2012/086671.

[0401] A compound MM20 was synthesized according to a synthesis method described in JP-A No. 2004-143419.

##STR00157## ##STR00158## ##STR00159##

<Synthesis Example 13> Synthesis of Compound Ma3

[0402] ##STR00160##

[0403] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, a compound Ma2 (64.6 g) and tetrahydrofuran (615 mL) were added, and the mixture was cooled down to −70° C. Into this, a n-butyllithium hexane solution (1.6 M, 218 mL) was dropped over a period of 1 hour, then, the mixture was stirred at −70° C. for 2 hours. To this, a compound Ma1 (42.1 g) was added in several batches, then, the mixture was stirred at −70° C. for 2 hours. Into this, methanol (40 mL) was dropped over a period of 1 hour, then, the mixture was heated up to room temperature. Thereafter, the solvent was distilled off by concentrating under reduced pressure, and toluene and water were added. Thereafter, an aqueous layer was separated and the resultant organic layer was washed with water. The resultant organic layer was concentrated under reduced pressure, and the resultant residue was purified by using a silica gel column (developing solvent: a mixed solvent of hexane and ethyl acetate), thereby obtaining 71 g of a compound Ma3 as colorless oil. The compound Ma3 had an HPLC area percentage value (UV: 254 nm) of 97.5%. This operation was repeated, to obtain a necessary amount of the compound Ma3.

[0404] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 2.43 (1H, s), 3.07-3.13 (4H, m), 6.95 (1H, d), 7.07 (1H. s), 7.18-7.28 (3H, m), 7.28-7.40 (4H, m), 7.66 (2H, s).

<Synthesis Example 14> Synthesis of Compound Ma4

[0405] ##STR00161##

[0406] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, the compound Ma3 (72.3 g), toluene (723 mL) and triethylsilane (118.0 g) were added, and the mixture was heated up to 70° C. Into this, methanesulfonic acid (97.7 g) was dropped over a period of 1.5 hours, then, the mixture was stirred at 70° C. for 0.5 hours. Thereafter, the mixture was cooled down to room temperature, and toluene (1 L) and water (1 L) were added, then, an aqueous layer was separated. The resultant organic layer was washed with water, 5% by weight sodium hydrogen carbonate water and water in this order. The resultant organic layer was concentrated under reduced pressure, and the resultant crude product was recrystallized from a mixed solvent of toluene and ethanol, thereby obtaining 51.8 g of a compound Ma4 as a white solid. This operation was repeated, thereby obtaining a necessary amount of the compound Ma4.

[0407] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 3.03-3.14 (4H, m), 4.99 (1H, s), 6.68 (1H, s), 6.92-7.01 (2H, m), 7.20-7.28 (2H, m), 7.29-7.38 (4H, m), 7.78 (2H, d).

<Synthesis Example 15> Synthesis of Compound Mb3

[0408] ##STR00162##

[0409] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, a compound Mb1 (185.0 g), a compound Mb2 (121.1 g), copper(i) iodide (3.2 g), dichloromethane (185 mL) and triethylamine (2.59 L) were added, and the mixture was heated up to the reflux temperature. Thereafter, the mixture was stirred at the reflux temperature for 0.5 hours, and cooled down to room temperature. To this was added dichloromethane (1.85 L), then, the mixture was filtrated through a filter paved with celite. To the resultant filtrate was added a 10% by weight sodium hydrogen carbonate aqueous solution, then, an aqueous layer was separated. The resultant organic layer was washed with water twice, washed with saturated NaCl water, then, magnesium sulfate was added. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant residue was purified by using a silica gel column (developing solvent: a mixed solvent of chloroform and ethyl acetate), thereby obtaining a crude product. The resultant crude product was dissolved in ethanol (1.4 L), then, activated carbon (5 g) was added, and the mixture was filtrated. The resultant filtrate was concentrated under reduced pressure, and the resultant residue was recrystallized from hexane, thereby obtaining 99.0 g of a compound Mb3 as a white solid. This operation was repeated, thereby obtaining a necessary amount of the compound Mb3.

[0410] .sup.1H-NMR (DMSO-d6, 300 MHz): δ (ppm): 1.52-1.55 (8H, m), 2.42 (4H, t), 3.38-3.44 (4H, m), 4.39-4.43 (2H, m), 7.31 (4H, s).

<Synthesis Example 16> Synthesis of Compound Mb4

[0411] ##STR00163##

[0412] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, the compound Mb3 (110.0 g), ethanol (1.65 L) and palladium/carbon (Pd weight: 10%) (11.0 g) were added, and the mixture was heated up to 30° C. Thereafter, a gas in the flask was purged with a hydrogen gas. Thereafter, the mixture was stirred at 30° C. for 3 hours while feeding a hydrogen gas into the flask. Thereafter, a gas in the flask was purged with a nitrogen gas. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant residue was purified by using a silica gel column (developing solvent: a mixed solvent of chloroform and ethyl acetate), thereby obtaining a crude product. The resultant crude product was recrystallized from hexane, thereby obtaining 93.4 g of a compound Mb4 as a white solid.

[0413] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 1.30-1.40 (8H, m), 1.55-1.65 (8H, m), 2.58 (4H, t), 3.64 (4H, t), 7.09 (4H, s).

[0414] .sup.13C-NMR (CDCl.sub.3, 75 MHz): δ (ppm): 25.53, 28.99, 31.39, 32.62, 35.37, 62.90, 128.18, 139.85.

<Synthesis Example 17> Synthesis of Compound Mb5

[0415] ##STR00164##

[0416] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, the compound Mb4 (61.0 g), pyridine (0.9 g) and toluene (732 mL) were added, and the mixture was heated up to 60° C. Into this, thionyl chloride (91.4 g) was dropped over a period of 1.5 hours, then, the mixture was stirred at 60° C. for 5 hours. The resultant mixture was cooled down to room temperature, then, concentrated under reduced pressure. The resultant residue was purified by using a silica gel column (developing solvent: a mixed solvent of hexane and ethyl acetate), thereby obtaining 64.3 g of a compound Mb5 as colorless oil.

[0417] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 1.35-1.40 (4H, m), 1.41-1.50 (4H, m), 1.60-1.68 (4H, m), 1.75-1.82 (4H, m), 2.60 (4H, t), 3.55 (4H, t), 7.11 (4H, s).

<Synthesis Example 18> Synthesis of Compound Mb6

[0418] ##STR00165##

[0419] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, the compound Mb5 (42.0 g), an iron powder (1.7 g), iodine (0.3 g) and dichloromethane (800 mL) were added. Thereafter, the whole flask was light-shielded, and cooled at 0 to 5° C. Into this, a mixed liquid of bromine (44.7 g) and dichloromethane (200 mL) was dropped over a period of 1 hour, then, the mixture was stirred at 0 to 5° C. overnight. The resultant mixed liquid was added to water (1.2 L) cooled at 0 to 5° C., then, an organic layer was separated. The resultant organic layer was washed with a 10% by weight sodium thiosulfate aqueous solution, and further, washed with saturated sodium chloride water and water in this order. To the resultant organic layer was added sodium sulfate, then, the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant residue was purified by using a silica gel column (developing solvent; hexane), thereby obtaining a crude product. The resultant crude product was recrystallized from hexane, thereby obtaining 47.0 g of a compound Mb6 as a white solid.

[0420] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 1.38-1.45 (4H, m), 1.47-1.55 (4H, m), 1.57-1.67 (4H, m), 1.77-1.84 (4H, m), 2.66 (4H, t), 3.55 (4H, t), 7.36 (2H, s).

<Synthesis Example 19> Synthesis of Compound Mb7

[0421] ##STR00166##

[0422] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, sodium iodide (152.1 g) and acetone (600 mL) were added, and the mixture was stirred at room temperature for 0.5 hours. To this was added Mb6 (40.0 g), then, the mixture was heated up to the reflux temperature, and stirred at the reflux temperature for 24 hours. Thereafter, the mixture was cooled down to room temperature, and the resultant mixed liquid was added to water (1.2 L). The deposited solid was separated by filtration, then, washed with water, thereby obtaining a crude product. The resultant crude product was recrystallized from a mixed liquid of toluene and methanol, thereby obtaining 46.0 g of a compound Mb7 as a white solid. This operation was repeated, thereby obtaining a necessary amount of the compound Mb7.

[0423] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 1.35-1.50 (8H, m), 1.57-1.65 (4H, m), 1.80-1.89 (4H, m), 2.65 (4H, t), 3.20 (4H, t), 7.36 (2H, s).

<Synthesis Example 20> Synthesis of Compound Mb8

[0424] ##STR00167##

[0425] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, sodium hydride (60% by weight, dispersed in liquid paraffin) (9.4 g), tetrahydrofuran (110 mL) and the compound Mb7 (63.2 g) were added. To this, a compound Ma4 (55.0 g) was added in several batches, then, the mixture was stirred for 12 hours. To this were added toluene (440 mL) and water (220 mL), then, an aqueous layer was separated. The resultant organic layer was washed with water, then, magnesium sulfate was added. The resultant mixed liquid was filtrated, and the resultant filtrate was concentrated under reduced pressure, thereby obtaining a crude product. The resultant crude product was purified by using a silica gel column (developing solvent: a mixed solvent of hexane and toluene). Thereafter, the product was recrystallized from hexane, thereby obtaining 84.1 g of a compound Mb8 as a white solid.

[0426] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 0.70-0.76 (4H, m), 1.10-1.21 (8H, m), 1.32-1.44 (4H, m), 2.39-2.58 (8H, m), 3.00-3.12 (8H, m), 6.82-6.94 (4H, m), 7.00-7.05 (2H, m), 7.17-7.28 (10H, m), 7.30-7.38 (4H, m), 7.71-7.77 (4H, m).

<Synthesis Example 21> Synthesis of Compound MM16

[0427] ##STR00168##

[0428] A gas in a flask equipped with a stirrer was purged with a nitrogen gas, then, the compound Mb8 (84.0 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (PdCl.sub.2(dppf).CH.sub.2Cl.sub.2, 2.2 g), bispinacolatodiboron (68.3 g), potassium acetate (52.8 g) and cyclopentyl methyl ether (840 mL) were added, and the mixture was heated up to the reflux temperature, then, stirred at the reflux temperature for 5 hours. Thereafter, the mixture was cooled down to room temperature, and toluene (500 mL) and water (300 mL) were added, then, an aqueous layer was separated. The resultant organic layer was washed with water, then, activated carbon (18.5 g) was added. The resultant mixed liquid was filtrated, and the resultant filtrate was concentrated under reduced pressure, thereby obtaining a crude product. The resultant crude product was purified by using a silica gel column (developing solvent: a mixed solvent of hexane and toluene). Thereafter, an operation of recrystallizing from a mixed solvent of toluene and acetonitrile was repeated, thereby obtaining 45.8 g of a compound MM1 as a white solid.

[0429] .sup.1H-NMR (CDCl.sub.3, 300 MHz): δ (ppm): 0.70-0.76 (4H, m), 1.24-1.40 (36H, m), 2.39-2.48 (4H, m), 2.66-2.75 (4H, m), 3.00-3.10 (8H, m), 6.76-6.90 (4H, m), 7.00-7.05 (2H, m), 7.19-7.30 (8H, m), 7.30-7.36 (4H, m), 7.43 (2H, s), 7.72 (4H, d).

<Synthesis Example 22> Synthesis of Compound MM18-st1

[0430] ##STR00169##

[0431] An argon gas atmosphere was prepared in a reaction vessel, then, the compound MM4-st2 (54.0 g) and tetrahydrofuran (470 mL) were added, and the mixture was cooled down to −70° C. Thereafter, into this was dropped a solution (1.02 mol/L, 200 mL) prepared by dissolving sec-butyllithium in hexane over a period of 1 hour. Thereafter, into this was dropped a solution prepared by dissolving the compound MM18-st0 (32.0 g) in tetrahydrofuran (64 mL). Thereafter, into this was dropped methanol (30 mL), then, the mixture was heated up to room temperature. The resultant reaction mixture was concentrated under reduced pressure, then, toluene and dilute hydrochloric acid water were added, and an aqueous layer and an organic layer were separated. The resultant organic layer was further washed with water. The resultant organic layer was concentrated under reduced pressure, and the resultant residue was dissolved in heptane (450 mL), then, activated carbon (22.3 g) was added, and the mixture was stirred. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain a crude product. The resultant crude product was washed in ethanol while grinding, to obtain 37.1 g of a compound MM18-st1 as a white solid. This operation was repeated, to obtain a necessary amount of the compound MM18-st1.

[0432] LC-MS (ESI, positive): [M+K].sup.+ 725

<Synthesis Example 23> Synthesis of Compound MM18

[0433] ##STR00170##

[0434] An argon gas atmosphere was prepared in a reaction vessel, then, the compound MM18-st1 (37.0 g) and methylene chloride (185 mL) were added, and the mixture was cooled down to 0° C. Thereafter, into this was dropped a BF.sub.3.diethyl ether complex (95 g) over a period of 0.5 hours, then, the mixture was heated up to room temperature. To the resultant reaction mixture was added water, and an aqueous layer and an organic layer were separated. The resultant organic layer was washed with 10% by weight potassium phosphate water, and the resultant organic layer was further washed with water. To the resultant organic layer was added magnesium sulfate, and the mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure. The resultant residue was dissolved in a mixed solvent of toluene and heptane, then, activated carbon (14.7 g) was added. The resultant mixture was filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain 42.3 g of a crude product. The crude product (57.2 g) obtained by repeating this operation was washed in a mixed solvent of ethanol and toluene while grinding, to obtain a white solid. The resultant white solid was recrystallized from a mixed solvent of butyl acetate and methanol, to obtain a white solid. The resultant white solid was recrystallized from a mixed solvent of toluene and methanol, to obtain a white solid. The resultant white solid was washed in acetonitrile while grinding, to obtain 25.5 g of a compound MM18 as a white solid.

[0435] LC-MS (ESI, positive): [M+K].sup.+ 707

[0436] .sup.1H-NMR (CDCl.sub.3, 300 MHz) δ (ppm): 0.97 (s, 18H), 1.56 (dd, 2H), 1.75 (dd, 2H), 2.71 (dd, 2H), 3.28 (dd, 2H), 3.47 (m, 2H), 6.79 (s, 2H), 6.91 (d, 2H), 6.98 (dd, 2H), 7.41-7.52 (m, 4H), 7.55 (d, 2H).

<Example 1> Synthesis of Polymer Compound 1

[0437] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.3 g), the compound MM12 (1.1 g), the compound MM13 (70 mg), the compound MM15 (80 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.3 mg) and toluene (42 mL) were added, and the mixture was heated at 105° C.

[0438] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (27 mL), and the mixture was refluxed for 8 hours.

[0439] (Step 3) After the reaction, to this were added the compound MM1 (138 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.3 mg), and the mixture was refluxed for 14 hours.

[0440] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.5 g of a polymer compound 1. The polymer compound 1 had a Mn of 4.7×10.sup.4 and a Mw of 1.5×10.sup.5.

[0441] The polymer compound 1 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12, a constitutional unit derived from the compound MM13 and a constitutional unit derived from the compound MM15 at a molar ratio of 50:40:5:5 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM1.

##STR00171##

[wherein, * represents a position binding to an adjacent constitutional unit.].

<Example 2> Synthesis of Polymer Compound 2

[0442] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.1 g), the compound MM12 (0.92 g), the compound MM13 (58 mg), the compound MM15 (66 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg) and toluene (35 mL) were added, and the mixture was heated at 105° C.

[0443] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (22 mL), and the mixture was refluxed for 5 hours.

[0444] (Step 3) After the reaction, to this were added the compound MM2 (182 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg), and the mixture was refluxed overnight.

[0445] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.2 g of a polymer compound 2. The polymer compound 2 had a Mn of 4.7×10.sup.4 and a Mw of 1.5×10.sup.5.

[0446] The polymer compound 2 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12, a constitutional unit derived from the compound MM13 and a constitutional unit derived from the compound MM15 at a molar ratio of 50:40:5:5 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM2.

##STR00172##

[wherein, * represents a position binding to an adjacent constitutional unit.]

<Example 3> Synthesis of Polymer Compound 3

[0447] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.1 g), the compound MM12 (0.92 g), the compound MM15 (133 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg) and toluene (36 mL) were added, and the mixture was heated at 105° C.

[0448] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (22 mL), and the mixture was refluxed for 5 hours.

[0449] (Step 3) After the reaction, to this were added the compound MM3 (218 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg), and the mixture was refluxed overnight.

[0450] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.3 g of a polymer compound 3. The polymer compound 3 had a Mn of 5.0×10.sup.4 and a Mw of 1.5×10.sup.5.

[0451] The polymer compound 3 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12 and a constitutional unit derived from the compound MM15 at a molar ratio of 50:40:10 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM3.

##STR00173##

[wherein, * represents a position binding to an adjacent constitutional unit].

<Example 4> Synthesis of Polymer Compound 4

[0452] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.1 g), the compound MM12 (0.92 g), the compound MM15 (133 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg) and toluene (36 mL) were added, and the mixture was heated at 105° C.

[0453] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (22 mL), and the mixture was refluxed for 5 hours.

[0454] (Step 3) After the reaction, to this were added the compound MM2 (181 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg), and the mixture was refluxed overnight.

[0455] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.3 g of a polymer compound 4. The polymer compound 4 had a Mn of 5.1×10.sup.4 and a Mw of 1.6×10.sup.5.

[0456] The polymer compound 4 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12 and a constitutional unit derived from the compound MM15 at a molar ratio of 50:40:10 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM2.

##STR00174##

[wherein, * represents a position binding to an adjacent constitutional unit.].

<Example 5> Synthesis of Polymer Compound 5

[0457] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (0.88 g), the compound MM16 (129 mg), the compound MM17 (62 mg), the compound MM12 (1.1 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg) and toluene (35 mL) were added, and the mixture was heated at 105° C.

[0458] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (23 mL), and the mixture was refluxed for 7.5 hours.

[0459] (Step 3) After the reaction, to this were added the compound MM1 (115 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg), and the mixture was refluxed overnight.

[0460] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.3 g of a polymer compound 5. The polymer compound 5 had a Mn of 3.9×10.sup.4 and a Mw of 1.5×10.sup.5.

[0461] The polymer compound 5 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM16, a constitutional unit derived from the compound MM17 and a constitutional unit derived from the compound MM12 at a molar ratio of 40:5:5:50 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM1.

##STR00175## [0462] [wherein, * represents a position binding to an adjacent constitutional unit.].

<Example 6> Synthesis of Polymer Compound 6

[0463] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.1 g), the compound MM12 (0.92 g), the compound MM13 (58 mg), the compound MM18 (84 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg) and toluene (36 mL) were added, and the mixture was heated at 105° C.

[0464] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (23 mL), and the mixture was refluxed for 7 hours.

[0465] (Step 3) After the reaction, to this were added the compound MM4 (150 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg), and the mixture was refluxed for 16 hours.

[0466] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.2 g of a polymer compound 6. The polymer compound 6 had a Mn of 4.9×10.sup.4 and a Mw of 1.5×10.sup.5.

[0467] The polymer compound 6 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12, a constitutional unit derived from the compound MM13 and a constitutional unit derived from the compound MM18 at a molar ratio of 50:40:5:5 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM4.

##STR00176##

[wherein, * represents a position binding to an adjacent constitutional unit.].

<Comparative Example 1> Synthesis of Polymer Compound C1

[0468] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.1 g), the compound MM12 (920 mg), the compound MM13 (58 mg), the compound MM15 (67 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg) and toluene (35 mL) were added, and the mixture was heated at 105° C.

[0469] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (22 mL), and the mixture was refluxed for 6 hours.

[0470] (Step 3) After the reaction, to this were added phenylboronic acid (61 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.1 mg), and the mixture was refluxed for 18 hours.

[0471] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.3 g of a polymer compound C1. The polymer compound C1 had a Mn of 4×10.sup.4 and a Mw of 1.4×10.sup.5.

[0472] The polymer compound C1 is a copolymer constituted of a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12, a constitutional unit derived from the compound MM13 and a constitutional unit derived from the compound MM15 at a molar ratio of 50:40:5:5 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from phenylboronic acid.

##STR00177##

[wherein, * represents a position binding to an adjacent constitutional unit.].

<Comparative Example 2> Synthesis of Polymer Compound C2

[0473] (Step 1) An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM11 (1.3 g), the compound MM12 (1.1 g), the compound MM10 (72 mg), the compound MM14 (85 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.3 mg) and toluene (42 mL) were added, and the mixture was heated at 105° C.

[0474] (Step 2) Into the reaction liquid was dropped a 20% by weight tetraethylammonium hydroxide aqueous solution (27 mL), and the mixture was refluxed for 6 hours.

[0475] (Step 3) After the reaction, to this were added the compound MM1 (140 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.3 mg), and the mixture was refluxed for 17 hours.

[0476] (Step 4) The reaction liquid was cooled, then, washed with water once, with 10% by weight dilute hydrochloric acid water twice, with a 3% by weight ammonia aqueous solution twice and with water twice, and the resultant solution was dropped into methanol, to observe precipitation. The precipitate was dissolved in toluene and the solution was purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, the mixture was stirred, then, the resultant precipitate was isolated by filtration and dried, to obtain 1.3 g of a polymer compound C2. The polymer compound C2 had a Mn of 4.6×10.sup.4 and a Mw of 1.4×10.sup.5.

[0477] The polymer compound C2 is a copolymer constituted a constitutional unit derived from the compound MM11, a constitutional unit derived from the compound MM12, a constitutional unit derived from the compound MM10 and a constitutional unit derived from the compound MM14 at a molar ratio of 50:40:5:5 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from the compound MM1.

##STR00178##

[wherein, * represents a position binding to an adjacent constitutional unit].

<Synthesis Example 24> Synthesis of Polymer Compound E1

(Synthesis of Polymer Compound E1)

[0478] An inert gas atmosphere was prepared in a reaction vessel, then, the compound MM14 (9.0 g), the compound MM20 (1.3 g), the compound MM19 (13.4 g), tetraethylammonium hydroxide (43.0 g), palladium acetate (8 mg), tri(2-methoxyphenyl)phosphine (0.05 g) and toluene (200 mL) were added, and the mixture was stirred for 8 hours with heating at 90° C. Thereafter, to this was added phenylboronic acid (0.22 g), and the mixture was stirred for 14 hours with heating at 90° C. The resultant mixture was cooled, then, an aqueous layer was removed. To the resultant organic layer was added a sodium diethyldithiocarbamate aqueous solution, and the mixture was stirred, then, an aqueous layer was removed. The resultant organic layer was washed with water and 3% by weight acetic acid water. The resultant organic layer was poured into methanol to cause precipitation of a solid, then, the solid was isolated by filtration and again dissolved in toluene, and the solution was allowed to pass through a silica gel column and an alumina column. The eluted toluene solution containing the solid was collected, and the collected toluene solution was poured into methanol to cause precipitation of a solid. The solid isolated by filtration was dried in vacuum at 50° C., to obtain 12.5 g of a polymer compound E1. The polymer compound E1 had a Mw of 3.1×10.sup.5.

[0479] The polymer compound E1 is a copolymer constituted of a constitutional unit derived from the compound MM19, a constitutional unit derived from the compound MM14 and a constitutional unit derived from the compound MM20 at a molar ratio of 50:45:5 according to the theoretical values calculated from the amounts of the charged raw materials, the copolymer containing at the terminal a constitutional unit represented by the following formula derived from phenylboronic acid.

##STR00179##

[wherein, * represents a position binding to an adjacent constitutional unit.].

Evaluation Example 1 of Film Residual Ratio

[0480] The polymer compound 1 was dissolved in xylene, to prepare a 0.7% by weight xylene solution. On a glass substrate, this xylene solution was spin-coated to form a film with a thickness of 20 nm, then, the film was heated on a hot plate at 180° C. for 60 minutes in a nitrogen gas atmosphere. Thereafter, it was cooled down to room temperature, to fabricate a measurement sample 1-1.

[0481] Next, the light transmission of the measurement sample 1-1 was measured, and the minimum transmission (T.sub.1) of the measurement sample 1-1 was determined. T.sub.1 of the measurement sample 1-1 was 0.701. For the measurement, a light transmission measurement apparatus (manufactured by Varian, Inc., trade name: Cary 5E ultraviolet.visible spectral photometer) was used and the wavelength sweeping in measuring light transmission was from 300 to 600 nm.

[0482] Next, the measurement sample 1-1 was immersed in xylene, the mixture was stirred for 60 minutes, then, the product was taken out from xylene. Thereafter, the product was placed on a spin coater and dried by rotating at 1000 rpm for 10 seconds, to fabricate a measurement sample 1-2.

[0483] Next, the light transmission of the measurement sample 1-2 was measured and the minimum transmission (T.sub.2) of the measurement sample 1-2 was calculated in the same manner as for the measurement sample 1-1. T.sub.2 of the measurement sample 1-2 was 0.701.

[0484] The film residual ratio of a film using the polymer compound 1 was calculated using the following formula, to find a value of 100%. The results are shown in Table 6.

Film residual ratio (%)=(log.sub.eT.sub.2/log.sub.eT.sub.1)×100

Evaluation Example 2 of Film Residual Ratio

[0485] A measurement sample 2-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample 2-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound 2 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample 2-1 was 0.730. Next, a measurement sample 2-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample 2-2 was determined. T.sub.2 of the measurement sample 2-2 was 0.740. The film residual ratio of a film using the polymer compound 2 was calculated using the above-described formula, to find a value of 95.7%. The results are shown in Table 6.

Evaluation Example 3 of Film Residual Ratio

[0486] A measurement sample 3-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample 3-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound 3 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample 3-1 was 0.726. Next, a measurement sample 3-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample 3-2 was determined. T.sub.2 of the measurement sample 3-2 was 0.751. The film residual ratio of a film using the polymer compound 3 was calculated using the above-described formula, to find a value of 89.4%. The results are shown in Table 6.

Evaluation Example 4 of Film Residual Ratio

[0487] A measurement sample 4-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample 4-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound 4 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample 4-1 was 0.727. Next, a measurement sample 4-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample 4-2 was determined. T.sub.2 of the measurement sample 4-2 was 0.727. The film residual ratio of a film using the polymer compound 4 was calculated using the above-described formula, to find a value of 100%. The results are shown in Table 6.

Evaluation Example 5 of Film Residual Ratio

[0488] A measurement sample 5-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample 5-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound 5 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample 5-1 was 0.753. Next, a measurement sample 5-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample 5-2 was determined. T.sub.2 of the measurement sample 5-2 was 0.761. The film residual ratio of a film using the polymer compound 5 was calculated using the above-described formula, to find a value of 96.3. The results are shown in Table 6.

Evaluation Example 6 of Film Residual Ratio

[0489] A measurement sample 6-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample 6-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound 6 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample 6-1 was 0.723. Next, a measurement sample 6-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample 6-2 was determined. T.sub.2 of the measurement sample 6-2 was 0.724. The film residual ratio of a film using the polymer compound 6 was calculated using the above-described formula, to find a value of 99.6%. The results are shown in Table 6.

Evaluation Comparative Example 1 of Film Residual Ratio

[0490] A measurement sample C1-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample C1-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound C1 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample C1-1 was 0.702. Next, a measurement sample C1-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample C1-2 was determined. T.sub.2 of the measurement sample C1-2 was 0.755. The film residual ratio of a film using the polymer compound C1 was calculated using the above-described formula, to find a value of 79.4%. The results are shown in Table 6.

Evaluation Comparative Example 2 of Film Residual Ratio

[0491] A measurement sample C2-1 before immersion into xylene was fabricated and the minimum transmission (T.sub.1) of the measurement sample C2-1 was determined in the same manner as in Evaluation Example 1 of film residual ratio excepting that a polymer compound C2 was used instead of the polymer compound 1 in Evaluation Example 1 of film residual ratio. T.sub.1 of the measurement sample C2-1 was 0.702. Next, a measurement sample C2-2 after immersion into xylene was fabricated, and the minimum transmission (T.sub.2) of the measurement sample C2-2 was determined. T.sub.2 of the measurement sample C2-2 was 0.785. The film residual ratio of a film using the polymer compound C2 was calculated using the above-described formula, to find a value of 68.4%. The results are shown in Table 6.

TABLE-US-00006 TABLE 6 polymer film compound residual ratio Evaluation polymer  100% Example 1 compound 1 Evaluation polymer 95.7% Example 2 compound 2 Evaluation polymer 89.4% Example 3 compound 3 Evaluation polymer  100% Example 4 compound 4 Evaluation polymer 96.3% Example 5 compound 5 Evaluation polymer 99.6% Example 6 compound 6 Evaluation polymer 79.4% Comparative compound C1 Example 1 Evaluation polymer 68.4% Comparative compound C2 Example 2

[0492] These results show that the crosslinkability of the polymer compound 1 to the polymer compound 6 is more excellent than the crosslinkability of the polymer compound C1 and the polymer compound C2 because the film residual ratio of a film using the polymer compound 1 to the polymer compound 6 is more excellent than the film residual ratio of a film using the polymer compound C1 and the polymer compound C2.

<Example D1> Fabrication and Evaluation of Light Emitting Device D1

(Formation of Anode and Hole Injection Layer)

[0493] A glass substrate was attached with an ITO film with a thickness of 45 nm by a sputtering method, to form an anode. On the anode, a polythiophene.sulfonic acid type hole injection agent AQ-1200 (manufactured by Plextronics) was spin-coated to form a film with a thickness of 35 nm, and the film was heated on a hot plate at 170° C. for 15 minutes under an air atmosphere, to form a hole injection layer.

(Formation of Hole Transporting Layer)

[0494] The polymer compound 1 was dissolved at a concentration of 0.7% by weight in xylene. The resultant xylene solution was spin-coated on the hole injection layer to form a film with a thickness of 20 nm, and the film was heated on a hot plate at 180° C. for 30 minutes under a nitrogen gas atmosphere, to form a hole transporting layer.

(Formation of Light Emitting Layer)

[0495] The polymer compound E1 was dissolved at a concentration of 1.1% by weight in xylene. The resultant xylene solution was spin-coated on the hole transporting layer to form a film with a thickness of 60 nm, and the film was heated on a hot plate at 150° C. for 10 minutes under a nitrogen gas atmosphere, to form a light emitting layer.

(Formation of Cathode)

[0496] The substrate carrying the light emitting layer formed thereon was placed in a vapor deposition machine and the internal pressure thereof was reduced to 1×10.sup.−4 Pa or less, then, as a cathode, sodium fluoride was vapor-deposited with a thickness of about 7 nm on the light emitting layer, then, aluminum was vapor-deposited with a thickness of about 120 nm on this. After vapor deposition, sealing with a glass substrate was performed, to fabricate a light emitting device D1.

(Evaluation of Light Emitting Device)

[0497] When voltage was applied to the light emitting device D1, EL light emission having a peak at 450 nm was observed. The external quantum efficiency (EQE) of the light emitting device D1 at 1000 cd/m.sup.2 was 5.8%. The current value was set so that the initial luminance was 5000 cd/m.sup.2, then, the device was driven at constant current and the temporal change of luminance was measured. As a result, the time (LT50) until the luminance became 50% of the initial luminance was 10.7 hours.

Example CD1: Fabrication and Evaluation of Light Emitting Device CD1

[0498] A light emitting device CD1 was fabricated in the same manner as in Example D1 excepting that a polymer compound C1 was used instead of the polymer compound 1 in Example D1.

[0499] When voltage was applied to the light emitting device CD1, EL light emission having a peak at 450 nm was observed. The external quantum efficiency (EQE) of the light emitting device CD1 at 1000 cd/m.sup.2 was 5.2%. The current value was set so that the initial luminance was 5000 cd/m.sup.2, then, the device was driven at constant current and the temporal change of luminance was measured. As a result, the time (LT50) until the luminance became 50% of the initial luminance was 7.9 hours.

Example CD2: Fabrication and Evaluation of Light Emitting Device CD2

[0500] A light emitting device CD2 was fabricated in the same manner as in Example D1 excepting that a polymer compound C2 was used instead of the polymer compound 1 in Example D1.

[0501] When voltage was applied to the light emitting device CD2, EL light emission having a peak at 450 nm was observed. The external quantum efficiency (EQE) of the light emitting device CD2 at 1000 cd/m.sup.2 was 4.0%. The current value was set so that the initial luminance was 5000 cd/m.sup.2, then, the device was driven at constant current and the temporal change of luminance was measured. As a result, the time (LT50) until the luminance became 50% of the initial luminance was 8.4 hours.

[0502] These results show that the external quantum efficiency and the luminance life of a light emitting device using the polymer compound 1 are more excellent than the external quantum efficiency and the luminance life of light emitting devices using the polymer compound C1 and the polymer compound C2 respectively.

INDUSTRIAL APPLICABILITY

[0503] According to the present invention, a polymer compound excellent in crosslinkability can be provided. Also, according to the present invention, a method for producing the polymer compound can be provided. Further, according to the present invention, a composition comprising the polymer compound and a light emitting device produced by using the polymer compound can be provided.