COMPOSITION AND LIGHT EMITTING DEVICE USING THE SAME

Abstract

A composition which is useful for providing a light emitting device having excellent light emission efficiency contains a compound represented by formula (C-1) and a phosphorescent compound represented by formula (1):

##STR00001##

Ring R.sup.1C to Ring R.sup.4C each represents an aromatic hydrocarbon ring or an aromatic hetero ring, R.sup.C represents a carbon, silicon, germanium, tin, or lead atom, and M represents a rhodium, palladium, iridium, or a platinum atom. n.sup.1 represents an integer of 1 or more, and n.sup.2 represents an integer of 0 or more. n.sup.1+n.sup.2 is 2 or 3. Ring R.sup.1A represents a triazole ring, Ring R.sup.2 represents an aromatic hydrocarbon ring or an aromatic hetero ring, E.sup.1, E.sup.2 and E.sup.11A to E.sup.13A represent a nitrogen atom or a carbon atom, R.sup.11A to R.sup.13A represent a hydrogen atom, an alkyl group, an aryl group, and A.sup.1-G.sup.1-A.sup.2 represents an anionic bidentate ligand.

Claims

1. A composition comprising a compound represented by the formula (C-1) and a phosphorescent compound represented by the formula (1), ##STR00071## wherein, Ring R.sup.1C, Ring R.sup.2C, Ring R.sup.1C and Ring R.sup.4C each independently represent an aromatic hydrocarbon ring or an aromatic hetero ring, and the foregoing rings optionally have a substituent, when a plurality of the substituents are present, they may be combined together to form a ring together with the atoms to which they are attached, R.sup.C represents a carbon atom, a silicon atom, a germanium atom, a tin atom or a lead atom, ##STR00072## wherein, M.sup.1 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom, n.sup.1 represents an integer of 1 or more, n.sup.2 represents an integer of 0 or more, and n.sup.1+n.sup.2 is 3 when M.sup.1 is a rhodium atom or an iridium atom, while n.sup.1+n.sup.2 is 2 when M.sup.1 is a palladium atom or a platinum atom, Ring R.sup.1A represents a triazole ring, Ring R.sup.2 represents an aromatic hydrocarbon ring or an aromatic hetero ring, and the foregoing rings optionally have a substituent, and when a plurality of the substituents are present, they may be combined together to form a ring together with the atoms to which they are attached, and when a plurality of Ring R.sup.2 are present, they may be the same or different, E.sup.1, E.sup.2, E.sup.11A, E.sup.12A and E.sup.13A each independently represent a nitrogen atom or a carbon atom, and when a plurality of E.sup.1, E.sup.2, E.sup.11A, E.sup.12A and E.sup.13A are present, they may be the same or different at each occurrence, and at least one of E.sup.1 and E.sup.2 is a carbon atom, R.sup.11A, R.sup.12A and R.sup.13A each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and the foregoing groups optionally have a substituent, and when a plurality of R.sup.11A, R.sup.12A and R.sup.13A are present, they may be the same or different at each occurrence, R.sup.11A and R.sup.12A may be combined together to form a ring together with the atoms to which they are attached, R.sup.12A and R.sup.13A may be combined together to form a ring together with the atoms to which they are attached, and the substituent which Ring R.sup.2 optionally has and R.sup.11A may be combined together to form a ring together with the atoms to which they are attached, when E.sup.11A is a nitrogen atom, R.sup.11A may be present or absent, when E.sup.12A is a nitrogen atom, R.sup.12A may be present or absent, and when E.sup.13A is a nitrogen atom, R.sup.13A may be present or absent, A.sup.1-G.sup.1-A.sup.2 represents an anionic bidentate ligand, A.sup.1 and A.sup.2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be a ring constituent atom, G.sup.1 represents a single bond or an atomic group constituting a bidentate ligand together with A.sup.1 and A.sup.2, and when a plurality of A.sup.1-G.sup.1-A.sup.2 are present, they may be the same or different.

2. The composition according to claim 1, wherein at least one of said Ring R.sup.1C, said Ring R.sup.2C, said Ring R.sup.3C and said Ring R.sup.4C has a group represented by the formula (D-1), ##STR00073## wherein, Ring R.sup.D represents an aromatic hydrocarbon ring or an aromatic hetero ring, and the foregoing rings optionally have a substituent, and when a plurality of the substituents are present, they may be combined together to form a ring together with the atoms to which they are attached, X.sup.D1 and X.sup.D2 each independently represent a single bond, an oxygen atom, a sulfur atom, a group represented by N(R.sup.XD1) or a group represented by C(R.sup.XD2).sub.2, R.sup.XD1 and R.sup.XD2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and the foregoing groups optionally have a substituent, and a plurality of R.sup.XD2 may be the same or different and may be combined together to form a ring together with the carbon atom to which they are attached, E.sup.1D, E.sup.2D and E.sup.3D each independently represent a nitrogen atom or a carbon atom, R.sup.1D, R.sup.2D and R.sup.3D each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and the foregoing groups optionally have a substituent, when E.sup.1D is a nitrogen atom, R.sup.1D is absent, when E.sup.2D is a nitrogen atom, R.sup.2D is absent, and when E.sup.3D is a nitrogen atom, R.sup.3D is absent, R.sup.1D and R.sup.2D may be combined together to form a ring together with the carbon atoms to which they are attached, R.sup.2D and R.sup.3D may be combined together to form a ring together with the carbon atoms to which they are attached, R.sup.1D and R.sup.XD1 may be combined together to form a ring together with the atoms to which they are attached, R.sup.1D and R.sup.XD2 may be combined together to form a ring together with the carbon atoms to which they are attached, the substituent which Ring R.sup.D optionally has and R.sup.XD1 may be combined together to form a ring together with the atoms to which they are attached, and the substituent which Ring R.sup.D optionally has and R.sup.XD2 may be combined together to form a ring together with the carbon atoms to which they are attached.

3. The composition according to claim 2, wherein the group represented by said formula (D-1) is a group represented by the formula (D-2), ##STR00074## wherein, X.sup.D1, X.sup.D2, E.sup.1D, E.sup.2D, E.sup.3D, R.sup.1D, R.sup.2D and R.sup.3D represent the same meaning as described above, E.sup.D, E.sup.D, E.sup.6D and E.sup.7D each independently represent a nitrogen atom or a carbon atom, R.sup.4D, R.sup.5D, R.sup.6D and R.sup.7D each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and the foregoing groups optionally have a substituent, when E.sup.4D is a nitrogen atom, R.sup.4D is absent, when E.sup.5D is a nitrogen atom, R.sup.5D is absent, when E.sup.6D is a nitrogen atom, R.sup.6D is absent, and when E.sup.7D is a nitrogen atom, R.sup.7D is absent, and R.sup.4D and R.sup.5D, R.sup.5D and R.sup.6D, R.sup.6D and R.sup.7D, R.sup.4D and R.sup.XD1, R.sup.4D and R.sup.XD2, R.sup.7D and R.sup.XD1, and R.sup.7D and R.sup.XD2 each may be combined together to form a ring together with the atoms to which they are attached.

4. The composition according to claim 1, wherein the compound represented by said formula (C-1) is a compound represented by the formula (C-2), ##STR00075## wherein, R.sup.C represents the same meaning as described above, E.sup.11C, E.sup.12C, E.sup.13C, E.sup.14C, E.sup.21C, E.sup.22C, E.sup.23C, E.sup.24C, E.sup.31C, E.sup.32C, E.sup.33C, E.sup.34C, E.sup.41C, E.sup.42C, E.sup.43C and E.sup.44C each independently represent a nitrogen atom or a carbon atom, Ring R.sup.1C, Ring R.sup.2C, Ring R.sup.3C and Ring R.sup.4C each independently represent a benzene ring, a pyridine ring or a diazabenzene ring, R.sup.11C, R.sup.12C, R.sup.13C, R.sup.14C, R.sup.21C, R.sup.22C, R.sup.23C, R.sup.24C, R.sup.31C, R.sup.32C, R.sup.33C, R.sup.34C, R.sup.41C, R.sup.42C, R.sup.43C and R.sup.44C each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and the foregoing groups optionally have a substituent, when E.sup.11C is a nitrogen atom, R.sup.11C is absent, when E.sup.12c is a nitrogen atom, R.sup.12c is absent, when E.sup.13c is a nitrogen atom, R.sup.13c is absent, when E.sup.14c is a nitrogen atom, R.sup.14c is absent, when E.sup.21c is a nitrogen atom, R.sup.21c is absent, when E.sup.22C is a nitrogen atom, R.sup.22c is absent, when E.sup.23C is a nitrogen atom, R.sup.23C is absent, when E.sup.24C is a nitrogen atom, R.sup.24C is absent, when E.sup.31c is a nitrogen atom, R.sup.31c is absent, when E.sup.32C is a nitrogen atom, R.sup.32c is absent, when E.sup.33C is a nitrogen atom, R.sup.33c is absent, when E.sup.34c is a nitrogen atom, R.sup.34c is absent, when E.sup.41c is a nitrogen atom, R.sup.41c is absent, when E.sup.42c is a nitrogen atom, R.sup.42c is absent, when E.sup.43C is a nitrogen atom, R.sup.43c is absent, and when E.sup.44C is a nitrogen atom, Rac is absent, and R.sup.11c and R.sup.12c, R.sup.12c and R.sup.13c, R.sup.13c and R.sup.14c, R.sup.14C and R.sup.34c, R.sup.34c and R.sup.33c, R.sup.33c and R.sup.32C, R.sup.32c and R.sup.31c, R.sup.31c and R.sup.41c, R.sup.41c and R.sup.42c, R.sup.42c and R.sup.43c, R.sup.43c and R.sup.44C, R.sup.44c and R.sup.24c, R.sup.24c and R.sup.23C, R.sup.23C and R.sup.22C, R.sup.22C and R.sup.21c, and R.sup.21C and R.sup.11C each may be combined together to form a ring together with the carbon atoms to which they are attached.

5. The composition according to claim 4, wherein the compound represented by said formula (C-2) is a compound represented by the formula (C-3), ##STR00076## wherein, R.sup.C, R.sup.11C, R.sup.12C, R.sup.13C, R.sup.14C, R.sup.21C, R.sup.22C, R.sup.23C, R.sup.24C, R.sup.31C, R.sup.32C, R.sup.33C, R.sup.34C, R.sup.41C, R.sup.42C, R.sup.43C and R.sup.44C represent the same meaning as described above.

6. The composition according to claim 4, wherein at least one of said R.sup.11C, said R.sup.12C, said R.sup.14C, said R.sup.21C, said R.sup.22C, said R.sup.24C, said R.sup.31C, said R.sup.32C, said R.sup.34C, said R.sup.41C, said R.sup.42C and said R.sup.44C is a group represented by said formula (D-1).

7. The composition according to claim 1, wherein the phosphorescent compound represented by said formula (1) is a phosphorescent compound represented by the formula (1-A), ##STR00077## wherein, M.sup.1, n.sup.1, n.sup.2, Ring R.sup.1A, E.sup.1, E.sup.11A, E.sup.12A, E.sup.13A, R.sup.11A, R.sup.12A, R.sup.13A and A.sup.1-G.sup.1-A.sup.2 represent the same meaning as described above, Ring R.sup.2A represents a benzene ring, a pyridine ring or a diazabenzene ring, E.sup.21A, E.sup.22A, E.sup.23A and E.sup.24A each independently represent a nitrogen atom or a carbon atom, and when a plurality of E.sup.21A, E.sup.22A, E.sup.23A and E.sup.24A are present, they may be the same or different at each occurrence, and when E.sup.21A is a nitrogen atom, R.sup.21A is absent, when E.sup.22A is a nitrogen atom, R.sup.22A is absent, when E.sup.23A is a nitrogen atom, R.sup.23A is absent, when E.sup.24A is a nitrogen atom, R.sup.24A is absent, R.sup.21A, R.sup.22A, R.sup.23A and R.sup.24A each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and the foregoing groups optionally have a substituent, and when a plurality of R.sup.21A, R.sup.22A, R.sup.23A and R.sup.24A are present, they may be the same or different at each occurrence, and, R.sup.21A and R.sup.22A, R.sup.22A and R.sup.23A, R.sup.23A and R.sup.24A, and R.sup.11A and R.sup.21A each may be combined together to form a ring together with the atoms to which they are attached.

8. The composition according to claim 7, wherein the phosphorescent compound represented by said formula (1-A) is a phosphorescent compound represented by the formula (1-A1), a phosphorescent compound represented by the formula (1-A2) or a phosphorescent compound represented by the formula (1-A3), ##STR00078## wherein, M.sup.1, n.sup.1, n.sup.2, R.sup.11A, R.sup.12A, R.sup.13A, R.sup.21A, R.sup.22A, R.sup.23A, R.sup.24A and A.sup.1-G.sup.1-A.sup.2 represent the same meaning as described above.

9. A light emitting device comprising the composition according to claim 1.

Description

EXAMPLES

[0286] The present invention will be illustrated further in detail by examples below, but the present invention is not limited to these examples.

[0287] In examples, the polystyrene-equivalent number-average molecular weight (Mn) and the polystyrene-equivalent weight-average molecular weight (Mw) of polymer compounds were determined by the following size exclusion chromatography (SEC) using tetrahydrofuran as a mobile phase.

[0288] A polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 L of the solution was injected into SEC. The mobile phase was flowed at a flow rate of 1.0 mL/min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories Ltd.) was used. As a detector, a UV-VIS detector (trade name: UV-8320GPC manufactured by Tosoh Corp.) was used.

[0289] NMR was measured by the following method.

[0290] Five to ten mg of a measurement sample was dissolved in about 0.5 mL of deutero-chloroform (CDCl.sub.3), deutero-tetrahydrofuran, deutero-dimethyl sulfoxide, deutero-acetone, deutero-N,N-dimethylformamide, deutero-toluene, deutero-methanol, deutero-ethanol, deutero-2-propanol or deutero-methylene chloride, and NMR thereof was measured using an NMR apparatus (trade name: INOVA300 manufactured by Agilent, trade name: JNM-ECZ400S/L1 manufactured by JEOL RESONANCE, or trade name: AVANCE600 manufactured by Bruker).

[0291] As an indicator of the purity of the compound, high performance liquid chromatography (HPLC) area percentage value was used. This value is a value by HPLC (trade name: LC-20A manufactured by Shimadzu Corp.) at UV=254 nm unless otherwise stated. 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 mass, and 1 to 10 L of the solution was poured into HPLC depending on the concentration. As a mobile phase of HPLC, acetonitrile/tetrahydrofuran were used while changing the ratio thereof from 100/0 to 0/100 (volume ratio), and flowed at a flow rate of 1.0 mL/min. As a column, SUMIPAX ODS Z-CLUE (manufactured by Sumika Chemical Analysis Service, Ltd., internal diameter: 4.6 mm, length: 250 mm, particle size: 3 m) or an ODS column having the equivalent performance was used. As a detector, a photodiode array detector (trade name: SPD-M20A manufactured by Shimadzu Corp.) was used.

<Synthesis Example M1> Synthesis of Compounds M1 to M5 and Metal Complex RM1

[0292] Compounds M1, M2 and M3 were synthesized according to a method described in International Publication WO 2013/146806.

[0293] A compound M4 was synthesized according to a method described in JP-A No. 2012-33845.

[0294] A compound M5 was synthesized according to a method described in JP-A No. 2010-189630.

[0295] A metal complex RM1 was synthesized according to a method described in International Publication WO 2009/157424.

##STR00057## ##STR00058##

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1

[0296] An inert gas atmosphere was prepared in a reaction vessel, then, the compound M1 (0.800 g), the compound M2 (0.149 g), the compound M3 (1.66 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.4 mg) and toluene (45 mL) were added, and the mixture was heated at 100 C. Thereafter, a 20% by mass tetraethylammonium hydroxide aqueous solution (16 mL) was dropped into this, and the solution was refluxed for 7 hours. Thereafter, to this were added 2-ethylphenylboronic acid (90 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.3 mg), and the solution was refluxed for 17.5 hours. Thereafter, to this was added a sodium diethyldithiacarbamate aqueous solution, and the mixture was stirred at 85 C. for 2 hours. The resultant reaction liquid was cooled, then, washed with 3.6% by mass hydrochloric acid, 2.5% by mass ammonia water and water, respectively. The resultant solution was dropped into methanol, to generate a precipitate. The resultant precipitate was dissolved in toluene, and purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, and the mixture was stirred, then, the resultant precipitate was collected by filtration, and dried, to obtain 1.64 g of a polymer compound HTL-1. The polymer compound HTL-1 had an Mn of 3.510.sup.4 and an Mw of 2.210.sup.5.

[0297] The polymer compound HTL-1 is a copolymer constituted of a constitutional unit derived from the compound M1, a constitutional unit derived from the compound M2 and a constitutional unit derived from the compound M3 at a molar ratio of 40:10:50, according to the theoretical values calculated from the amounts of the charged raw materials.

<Synthesis Example HTL2> Synthesis of Polymer Compound HTL-2

[0298] An inert gas atmosphere was prepared in a reaction vessel, then, the compound M1 (2.52 g), the compound M2 (0.470 g), the compound M3 (4.90 g), the metal complex RM1 (0.530 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (4.2 mg) and toluene (158 mL) were added, and the mixture was heated at 100 C. Thereafter, a 20% by mass tetraethylammonium hydroxide aqueous solution (16 mL) was dropped into this, and the solution was refluxed for 8 hours. Thereafter, to this were added phenylboronic acid (116 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (4.2 mg), and the solution was refluxed for 15 hours. Thereafter, to this was added a sodium diethyldithiacarbamate aqueous solution, and the mixture was stirred at 85 C. for 2 hours. The resultant reaction liquid was cooled, then, washed with 3.6% by mass hydrochloric acid, 2.5% by mass ammonia water and water, respectively. The resultant solution was dropped into methanol, to generate a precipitate. The resultant precipitate was dissolved in toluene, and purified by passing through an alumina column and a silica gel column in this order. The resultant solution was dropped into methanol, and the mixture was stirred, then, the resultant precipitate was collected by filtration, and dried, to obtain 6.02 g of a polymer compound HTL-2. The polymer compound HTL-2 had an Mn of 3.810.sup.4 and an Mw of 4.510.sup.5.

[0299] The polymer compound HTL-2 is a copolymer constituted of a constitutional unit derived from the compound M1, a constitutional unit derived from the compound M2, a constitutional unit derived from the compound M3 and a constitutional unit derived from the metal complex RM1 at a molar ratio of 40:10:47:3, according to the theoretical values calculated from the amounts of the charged raw materials.

<Synthesis Examples B1 to B3 and B8> Synthesis and Acquisition of Phosphorescent Compounds B1 to B3 and B8

[0300] A phosphorescent compound B1 (FIrpic) was purchased from Aldrich.

[0301] A phosphorescent compound B2 was synthesized according to a method described in JP-A No. 2013-147551.

[0302] A phosphorescent compound B3 was synthesized with reference to a method described in International Publication WO 2016/185183.

[0303] A phosphorescent compound B8 was synthesized with reference to a method described in International Publication WO 2006/121811.

##STR00059##

<Synthesis Example B4> Synthesis of Phosphorescent Compound B4

[0304] ##STR00060##

(Synthesis of Compound L4-2)

[0305] A nitrogen gas atmosphere was prepared in a reaction vessel, then, a compound L4-1 (50 g) and N-methyl-2-pyrrolidone (200 mL) were added, and the mixture was stirred at 0 C. Thereafter, a compound L4-1 (40 g) dissolved in N-methyl-2-pyrrolidone (40 mL) was dropped into this, and the solution was stirred at room temperature for 18 hours. The resultant reaction liquid was poured into ion exchanged water (1.2 L), to generate a precipitate. The resultant precipitate was collected by filtration, then, washed with a 1 M hydrochloric acid aqueous solution, ion exchanged water and heptane in series. The resultant solid was dried under reduced pressure, to obtain a compound L4-2 (43 g, white solid).

[0306] The analysis results of the compound L4-2 were as described below.

[0307] .sup.1H-NMR (600 MHz, CDCl.sub.3): (ppm)=9.64 (br, 1H), 8.90 (br, 1H), 7.86 (d, 2H), 7.56 (t, 1H), 7.45 (t, 2H), 7.02-7.08 (m, 3H), 2.41 (s, 6H).

(Synthesis of Compound L4-3)

[0308] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L4-2 (43 g) and toluene (740 mL) were added, and the mixture was stirred at room temperature. Thereafter, to this was added phosphorus pentachloride (67 g), then, the mixture was stirred at 110 C. for 21 hours. The resultant reaction liquid was cooled down to room temperature, then, poured into ice water (500 mL), the mixture was stirred for 2 hours, then, an aqueous layer was removed. The resultant organic layer was washed with ion exchanged water and a 10% by mass sodium hydrogen carbonate aqueous solution, respectively. The resultant organic layer was dried over magnesium sulfate, then, filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a compound L4-3 (40 g).

(Synthesis of Compound L4-5)

[0309] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L4-3 (40 g), compound L4-4 (32 g) and xylene (800 mL) were added, and the mixture was stirred at room temperature. Thereafter, to this was added p-toluenesulfonic acid (3 g), and the mixture was stirred at 120 C. for 116 hours. The resultant reaction liquid was cooled down to room temperature, then, ion exchanged water (800 mL) was added, and the mixture was stirred at room temperature for 1 hour. An aqueous layer was removed from the resultant reaction liquid, then, the resultant organic layer was washed with a 5% by mass sodium hydrogen carbonate aqueous solution. The resultant organic layer was dried over magnesium sulfate, then, filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a coarse product. The resultant coarse product was purified by silica gel column chromatography (using a mixed solvent of heptane and ethyl acetate) and silica gel column chromatography (using acetonitrile and tetrahydrofuran) in series, to obtain a compound L4-5 (1.3 g, white solid). The HPLC area percentage value of the compound L4-5 was 99.5% or more. The above-described operation was conducted repeatedly, to obtain a necessary amount of the compound L4-5.

[0310] The analysis results of the compound L4-5 were as described below.

[0311] .sup.1H-NMR (600 MHz, THF-d.sub.8): (ppm)=7.42 (d, 2H), 7.30 (t, 1H), 7.24 (t, 2H), 7.15 (t, 1H), 6.98 (d, 2H), 6.85 (s, 2H), 2.51 (t, 2H), 2.07 (s, 6H), 1.81 (s, 6H), 1.56 (m, 2H), 1.26-1.32 (m, 6H), 0.88 (t, 3H).

(Synthesis of Phosphorescent Compound B4)

[0312] A nitrogen gas atmosphere was prepared in a reaction vessel, then, tris(acetylacetonato)iridium(III) (0.6 g), the compound L4-5 (2.0 g) and tridecane (2 mL) were added, and the mixture was stirred at 250 C. for 120 hours. The resultant reaction liquid was cooled down to room temperature, then, purified by silica gel column chromatography (using a mixed solvent of heptane and ethyl acetate), then, crystallized using a mixed solvent of methylene chloride and acetonitrile. The resultant solid was dried under reduced pressure, to obtain a phosphorescent compound B4 (0.6 g, yellow solid). The HPLC area percentage value of the phosphorescent compound B4 was 99.2%.

[0313] The analysis results of the phosphorescent compound B4 were as described below.

[0314] .sup.1H-NMR (600 MHz, THF-d.sub.8): (ppm)=7.04-7.08 (m, 6H), 6.93 (s, 3H), 6.92 (s, 3H), 6.88 (d, 3H), 6.84 (d, 3H), 6.61 (t, 3H), 6.43 (t, 3H), 6.29 (d, 3H), 2.57 (t, 6H), 2.12 (s, 9H), 1.95 (s, 9H), 1.82 (s, 9H), 1.70 (s, 9H), 1.62 (m, 6H), 1.28-1.36 (m, 18H), 0.89 (t, 9H).

<Synthesis Example B5> Synthesis of Phosphorescent Compound B5

[0315] ##STR00061##

(Synthesis of Reaction Mixture L5-1)

[0316] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L5-1 (50 g) and thionyl chloride (100 mL) were added, and the mixture was stirred for 3 hours under reflux. The resultant reaction mixture was cooled down to room temperature, then, thionyl chloride was distilled off under reduced pressure, to obtain a reaction mixture L5-1.

(Synthesis of Compound L5-2)

[0317] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L4-1 (47 g) and tetrahydrofuran (1 L) were added, and the mixture was cooled to 0 C. Thereafter, to this was added triethylamine (54 mL), and the mixture was stirred at 0 C. for 45 minutes. Thereafter, to this was added the reaction mixture L5-1 (total amount) obtained in (Synthesis of reaction mixture L5-1), and the mixture was stirred at room temperature for 16 hours. The resultant reaction liquid was filtrated, then, the resultant filtrate was concentrated under reduced pressure, to obtain a coarse product. The resultant coarse product was washed with a mixed solvent of ethyl acetate and hexane, then, dried under reduced pressure, to obtain a compound L5-2 (50 g). The HPLC area percentage value of the compound L5-2 was 95.2%. The above-described operation was conducted repeatedly, to obtain a necessary amount of the compound L5-2.

[0318] The analysis results of the compound L5-2 were as described below.

[0319] LC-MS (APCI, positive): m/z=263 [M+H].sup.+

[0320] .sup.1H-NMR (300 MHz, CDCl.sub.3): (ppm)=0.84 (t, 9H), 1.64 (q, 6H), 7.39-7.54 (m, 3H), 7.81-7.84 (m, 2H), 8.72-8.74 (m, 1H), 9.66-9.68 (m, 1H).

(Synthesis of Compound L5-3)

[0321] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L5-2 (58 g) and toluene (600 mL) were added, and the mixture was stirred at room temperature. Thereafter, to this was added phosphorus pentachloride (92 g), then, the mixture was stirred at 110 C. for 3 hours. The resultant reaction liquid was cooled down to room temperature, then, a compound L5-4 (78.2 g) and p-toluenesulfonic acid (3 g) were added, and the mixture was stirred at 130 C. for 4 days. The resultant reaction liquid was cooled down to room temperature, concentrated under reduced pressure, then, ethyl acetate (2 L) was added, and the liquid was washed with a 10% by mass sodium hydrogen carbonate aqueous solution. The resultant organic layer was dried over magnesium sulfate, then, filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain a coarse product. The resultant coarse product was purified by silica gel column chromatography (using a mixed solvent of methanol and chloroform), then, crystallized using acetonitrile, then, dried under reduced pressure, to obtain a compound L5-3 (6 g). The HPLC area percentage value of the compound L5-3 was 99.1%.

[0322] The analysis results of the compound L5-3 were as described below.

[0323] LC-MS (APCI, positive): m/z=404 [M+H]+

[0324] .sup.1H-NMR (400 MHz, CDCl.sub.3): (ppm)=0.83 (t, 9H), 1.34 (s, 9H), 1.64 (q, 6H), 1.96 (s, 6H), 7.12 (s, 2H), 7.20-7.23 (m, 2H), 7.28-7.34 (m, 3H).

(Synthesis of Phosphorescent Compound B5)

[0325] A nitrogen gas atmosphere was prepared in a reaction vessel, then, tris(acetylacetonato)iridium(III) (1.4 g), the compound L5-3 (4.6 g) and pentadecane (2 mL) were added, and the mixture was stirred at 300 C. for 18 hours. The resultant reaction liquid was cooled down to room temperature, dissolved in toluene, then, concentrated under reduced pressure, to obtain a coarse product. The resultant coarse product was purified by silica gel column chromatography (using a mixed solvent of heptane and ethyl acetate), then, crystallized using a mixed solvent of acetonitrile and toluene. The resultant solid was dried under reduced pressure, to obtain a phosphorescent compound B5 (2.8 g). The HPLC area percentage value of the phosphorescent compound B5 was 99.5% or more.

[0326] The analysis results of the phosphorescent compound B5 were as described below.

[0327] .sup.1H-NMR (600 MHz, THF-d.sub.8): (ppm)=7.30 (s, 6H), 6.90 (d, 3H), 6.44-6.48 (m, 3H), 6.22-6.26 (m, 3H), 5.77 (d, 3H), 2.10 (s, 9H), 1.89 (s, 9H), 1.56 (s, 18H), 1.38 (s, 27H), 0.73 (t, 27H).

<Synthesis Example B6> Synthesis of Phosphorescent Compound B6

[0328] ##STR00062##

(Synthesis of Compound L6-2)

[0329] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L4-1 (100 g), triethylamine (114 mL) and tetrahydrofuran (1.5 L) were added, and the mixture was stirred at 0 C. Thereafter, a compound L6-1 (52 mL) was dropped into this, then, the mixture was stirred at room temperature for 16 hours. The resultant reaction liquid was filtrated, then, the resultant filtrate was concentrated, to obtain a coarse product. The resultant coarse product was crystallized using ethyl acetate, then, dried under reduced pressure, to obtain a compound L6-2 (70 g). The HPLC area percentage value of the compound L6-2 was 98.7%.

[0330] The analysis results of the compound L6-2 were as described below.

[0331] LC-MS (APCI, positive): m/z=179 [M+H].sup.+

[0332] .sup.1H-NMR (300 MHz, DMSO-d.sub.6): (ppm)=10.26 (br, 1H), 9.86 (br, 1H), 7.83-7.86 (m, 2H), 7.45-7.56 (m, 3H), 1.90 (s, 3H).

(Synthesis of Compound L6-4)

[0333] A nitrogen gas atmosphere was prepared in a reaction vessel, then, the compound L6-2 (70 g) and xylene (700 mL) were added, and the mixture was stirred at room temperature. Thereafter, to this was added phosphorus pentachloride (123 g), and the mixture was stirred at 130 C. for 2 hours. The resultant reaction liquid was cooled down to room temperature, a compound L6-3 (70 g) was added, then, the mixture was stirred at 130 C. for 8 hours. The resultant reaction liquid was cooled down to room temperature, concentrated under reduced pressure, then, ethyl acetate was added. The resultant organic layer was washed with ion exchanged water, a 10% by mass sodium hydrogen carbonate aqueous solution and saturated saline in series. The resultant organic layer was dried over sodium sulfate, then, filtrated, and the resultant filtrate was concentrated under reduced pressure, to obtain a coarse product. The resultant coarse product was purified by silica gel column chromatography (using a mixed solvent of hexane and ethyl acetate), then, crystallized using a mixed solvent of N,N-dimethylformamide and water. The resultant solid was dried under reduced pressure, to obtain a compound L6-4 (70 g, white solid). The HPLC area percentage value of the compound L6-4 was 99.2-.

[0334] The analysis results of the compound L6-4 were as described below.

[0335] LC-MS (APCI, positive): m/z=320 [M+H]+

[0336] .sup.1H-NMR (400 MHz, CDCl.sub.3): (ppm)=7.53-7.58 (m, 1H), 7.48 (d, 2H), 7.33 (d, 2H), 7.28-7.30 (m, 1H), 7.21-7.25 (m, 2H), 2.39 (q, 2H), 2.26 (s, 3H), 1.14 (d, 6H), 0.87 (d, 6H).

(Synthesis of Phosphorescent Compound B6)

[0337] A nitrogen gas atmosphere was prepared in a reaction vessel, then, tris(acetylacetonato)iridium(III) (1.2 g), the compound L6-4 (4.0 g) and tridecane (1 mL) were added, and the mixture was stirred at 280 C. for 18 hours. The resultant reaction liquid was cooled down to room temperature, then, purified by silica gel column chromatography (using a mixed solvent of ethyl acetate and methanol), then, crystallized using a mixed solvent of toluene and acetonitrile. The resultant solid was dried under reduced pressure, to obtain a phosphorescent compound B6 (1.7 g, yellow solid). The HPLC area percentage value of the phosphorescent compound B6 was 99.5% or more.

[0338] The analysis results of the phosphorescent compound B6 were as described below.

[0339] .sup.1H-NMR (600 MHz, THF-d.sub.8): (ppm)=7.56 (t, 3H), 7.42 (dd, 3H), 7.40 (dd, 3H), 6.87 (dd, 3H), 6.52 (td, 3H), 6.35 (td, 3H), 6.17 (dd, 3H), 2.83 (hept, 3H), 2.34 (hept, 3H), 2.10 (s, 9H), 1.23 (d, 9H), 0.98 (d, 9H), 0.96 (d, 9H), 0.92 (d, 9H).

<Synthesis Example B7> Synthesis of Phosphorescent Compound B7

[0340] ##STR00063##

(Synthesis of Compound L7-3)

[0341] A nitrogen gas atmosphere was prepared in a reaction vessel, then, a compound L7-1 (21.4 g), triethylamine (13.0 mL) and tetrahydrofuran (300 mL) were added, and the mixture was cooled to 0 C. Thereafter, a compound L7-2 (12.8 mL) was dropped into this, and the mixture was stirred at room temperature for 16 hours. Thereafter, to this was added ion exchanged water (100 mL), to generate a precipitate. The reaction liquid containing the resultant precipitate was filtrated, to obtain a residue L7-3-1 and a filtrate L7-3-2.

[0342] The resultant residue L7-3-1 was washed with toluene, then, dried under reduced pressure, to obtain a solid L7-3 (24.5 g).

[0343] An aqueous layer was removed from the resultant filtrate L7-3-2, and the resultant organic layer was dried over magnesium sulfate, then, filtrated. The resultant filtrate was concentrated under reduced pressure, then, crystallized with a mixed solvent of toluene and heptane. The resultant solid was dried under reduced pressure, to obtain a solid L7-3 (3.9 g).

[0344] The resultant solid L7-3 and the solid L7-3 were combined, then, crystallized using a mixed solvent of toluene and heptane. The resultant solid was dried under reduced pressure, to obtain a compound L7-3 (27.8 g, white solid). The HPLC area percentage value of the compound L7-3 was 98.91.

[0345] The analysis results of the compound L7-3 were as described below.

[0346] .sup.1H-NMR (600 MHz, THF-d.sub.8): (ppm)=7.57 (d, 2H), 7.43 (t, 2H), 7.35 (s, 2H), 7.34 (t, 1H), 6.82 (brs, 1H), 3.08 (septet, 2H), 1.73 (q, 2H), 1.34 (s, 6H), 1.25 (d, 12H), 1.00 (t, 3H).

(Synthesis of Compound L7-5)

[0347] A compound L7-5 was synthesized with reference to a method described in Organic Letters, vol. 17, pp. 1184-1187, 2015 using the compound L7-3 (19.1 g), the compound L7-4 (9.0 g), chlorobenzene (150 mL), 2-fluoropyridine (5.15 mL) and trifluoromethanesulfonic anhydride (10.0 mL).

[0348] The analysis results of the compound L7-5 were as described below.

[0349] .sup.1H-NMR (600 MHz, CDCl.sub.3): (ppm)=7.68 (d, 2H), 7.52 (t, 2H), 7.50 (s, 2H), 7.43 (t, 1H), 7.26 (s, 1H), 7.05-6.98 (m, 3H), 2.53 (septet, 2H), 2.15 (s, 3H), 1.88 (q, 2H), 1.28 (d, 6H), 1.23 (s, 6H), 0.89 (t, 3H), 0.77 (d, 6H).

(Synthesis of Phosphorescent Compound B7)

[0350] A nitrogen gas atmosphere was prepared in a reaction vessel, then, tris(acetylacetonato)iridium(III)(0.72 g), the compound L7-5 (2.8 g) and pentadecane (2 mL) were added, and the mixture was stirred at 300 C. for 24 hours. The resultant reaction liquid was cooled down to room temperature, then, purified by silica gel column chromatography (using a mixed solvent of methylene chloride and ethyl acetate), and subsequently, crystallized in series using a mixed solvent of acetonitrile and toluene, a mixed solvent of toluene and methanol, and a mixed solvent of methylene chloride and acetonitrile. The resultant solid was washed with methylene chloride, then, dried under reduced pressure, to obtain a phosphorescent compound B7 (0.82 g). The HPLC area percentage value of the phosphorescent compound B7 was 98.8%.

[0351] The analysis results of the phosphorescent compound B7 were as described below.

[0352] .sup.1H-NMR (600 MHz, THF-d.sub.8): (ppm)=7.74 (d, 6H), 7.64 (dd, 6H), 7.48 (t, 6H), 7.38 (t, 3H), 6.68 (d, 3H), 6.30 (d, 3H), 5.62 (s, 3H), 2.94 (septet, 3H), 2.37 (septet, 3H), 1.75 (s, 9H), 1.71-1.64 (m, 6H), 1.34 (d, 9H), 1.22-1.17 (m, 27H), 0.98 (d, 9H), 0.90 (d, 9H), 0.81 (d, 9H).

<Synthesis Example G1, G2 and R1> Synthesis of Phosphorescent Compounds G1, G2 and R1

[0353] A phosphorescent compound G1 was synthesized with reference to a method described in International Publication WO 2009/131255.

[0354] A phosphorescent compound G2 was synthesized according to a method described in JP-A No. 2014-224101.

[0355] A phosphorescent compound R.sup.1 was synthesized with reference to a method described in JP-A No. 2006-188673.

##STR00064##

Synthesis Example HM-1, HM-5 to HM-7 and HM-9

[0356] Synthesis and acquisition of compounds HM-1, HM-5 to HM-7 and HM-9

[0357] A compound HM-1 was purchased from Luminescence Technology Corp.

[0358] A compound HM-5 was synthesized with reference to a method described in International Publication WO 2014/023388.

[0359] A compound HM-6 and a compound HM-7 were synthesized with reference to a method described in International Publication WO 2012/048820.

[0360] A compound HM-9 was synthesized with reference to a method described in International Publication WO 2013/045411.

##STR00065##

<Synthesis Example HM-2> Synthesis of Compound HM-2

[0361] ##STR00066##

[0362] A nitrogen gas atmosphere was prepared in a reaction vessel, then, a compound HM-2a (15.6 g), a compound HM-2b (10.3 g), toluene (390 mL), tetrakis(triphenylphosphine)palladium(0) (2.2 g) and a 20% by mass tetrabutylammonium hydroxide aqueous solution (194 g) were added, and the mixture was stirred at 90 C. for 4 hours. The resultant reaction liquid was cooled down to room temperature, then, filtrated through a filter paved with Celite. The resultant filtrate was washed with ion exchanged water, then, the resultant organic layer was dried over anhydrous sodium sulfate, and filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a solid. The resultant solid was crystallized using a mixed solvent of toluene and 2-propanol, then, dried at 50 C. under reduced pressure, to obtain a compound HM-2 (15.2 g). The HPLC area percentage value of the compound HM-2 was 99.5% or more.

[0363] The analysis results of the compound HM-2 were as described below.

[0364] .sup.1H-NMR (CD.sub.2Cl.sub.2, 400 MHz): (ppm)=6.70-6.83 (4H, m), 7.15 (3H, t), 7.39 (3H, t), 7.48 (3H, t), 7.59 (2H, t), 7.83-7.93 (4H, m), 8.18-8.23 (3H, m).

<Synthesis Example HM-3> Synthesis of Compound HM-3

[0365] ##STR00067##

[0366] A nitrogen gas atmosphere was prepared in a reaction vessel, then, a compound HM-3a (13.5 g), a compound HM-2b (8.9 g), toluene (404 mL), tetrakis(triphenylphosphine)palladium(0) (2.0 g) and a 20% by mass tetrabutylammonium hydroxide aqueous solution (166 g) were added, and the mixture was stirred at 90 C. for 3 hours. The resultant reaction liquid was cooled down to room temperature, then, filtrated through a filter paved with Celite. The resultant filtrate was washed with ion exchanged water, then, the resultant organic layer was dried over anhydrous sodium sulfate, and filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a solid. The resultant solid was purified by silica gel column chromatography (using a mixed solvent of hexane and chloroform), and further, crystallized using a mixed solvent of toluene and methanol, then, dried at 50 C. under reduced pressure, to obtain a compound HM-3 (10.5 g). The HPLC area percentage value of the compound HM-3 was 99.5% or more.

[0367] The analysis results of the compound HM-3 were as described below.

[0368] .sup.1H-NMR (CD.sub.2Cl.sub.2, 400 MHz): (ppm)=6.51 (1H, d), 6.60 (1H, d), 6.80 (4H, m), 6.92 (1H, t), 7.21 (3H, m), 7.34 (1H, d), 7.39-7.50 (4H, m), 7.65 (1H, d), 7.71 (1H, t), 7.81 (1H, d), 7.88 (2H, d), 8.28-8.35 (2H, m).

<Synthesis Example HM-4> Synthesis of Compound HM-4

[0369] ##STR00068##

[0370] A nitrogen gas atmosphere was prepared in a reaction vessel, then, a compound HM-4a (1.6 g), a compound HM-4b (1.3 g), xylene (63 mL), palladium(II) acetate (22 mg), tri-tert-butylphosphonium tetrafluoroborate (63 mg) and sodium tert-butoxide (1.9 g) were added, and the mixture was stirred for 54 hours under reflux with heat. The resultant reaction liquid was cooled down to room temperature, then, filtrated through a filter paved with silica gel and Celite. The resultant filtrate was washed with ion exchanged water, then, the resultant organic layer was dried over anhydrous sodium sulfate, and filtrated. The resultant filtrate was concentrated under reduced pressure, to obtain a solid. The resultant solid was purified by silica gel column chromatography (using a mixed solvent of hexane and chloroform), and further, crystallized using a mixed solvent of chloroform and 2-propanol, then, dried at 50 C. under reduced pressure, to obtain a compound HM-4 (1.0 g). The HPLC area percentage value of the compound HM-4 was 99.5% or more.

[0371] The analysis results of the compound HM-4 were as described below.

[0372] .sup.1H-NMR (CD.sub.2Cl.sub.2, 400 MHz): (ppm)=7.08 (4H, t), 7.34 (6H, m), 7.47-7.57 (12H, m), 8.02 (2H, d), 8.12 (2H, s), 8.22 (4H, d).

<Synthesis Example HM-8> Synthesis of Compound HM-8

[0373] ##STR00069##

[0374] A nitrogen gas atmosphere was prepared in a reaction vessel, then, a compound HM-2a (1.64 g), a compound HM-8b (1.00 g), toluene (40 mL), tetrakis(triphenylphosphine)palladium(0) (0.24 g) and a 20% by mass tetrabutylammonium hydroxide aqueous solution (20 g) were added, and the mixture was stirred at 90 C. for 3 hours. The resultant reaction liquid was cooled down to room temperature, then, toluene was added, and the liquid was washed with ion exchanged water. The resultant organic layer was dried over anhydrous magnesium sulfate, then, filtrated through a filter paved with silica gel and Celite. The resultant filtrate was concentrated under reduced pressure, to obtain a solid. The resultant solid was crystallized using a mixed solvent of toluene and 2-propanol, then, dried at 50 C. under reduced pressure, to obtain a compound HM-8 (1.7 g). The HPLC area percentage value of the compound HM-8 was 99.5% or more.

[0375] The analysis results of the compound HM-8 were as described below.

[0376] .sup.1H-NMR (CDCl.sub.3, 400 MHz): (ppm)=8.36 (d, 1H), 8.03-7.99 (m, 1H), 7.98-7.93 (m, 2H), 7.89-7.86 (m, 2H), 7.70-7.60 (m, 3H), 7.51-7.35 (m, 6H), 7.17-7.12 (m, 3H), 6.89 (d, 1H), 6.86-6.82 (m, 2H), 6.78 (d, 1H).

<Synthesis Example ETL1> Synthesis of Polymer Compound ETL-1

[0377] An inert gas atmosphere was prepared in a reaction vessel, then, the compound M4 (9.23 g), the compound M5 (4.58 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (8.6 mg), methyltrioctylammonium chloride (trade name: Aliquat336 (registered trademark) manufactured by Sigma Aldrich)(0.098 g) and toluene (175 mL) were added, and the mixture was heated at 105 C. Thereafter, a 12% by mass sodium carbonate aqueous solution (40.3 mL) was dropped into this, and the solution was refluxed for 29 hours. Thereafter, to this were added phenylboronic acid (0.47 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (8.7 mg), and the solution was refluxed for 14 hours. Thereafter, to this was added a sodium diethyldithiacarbamate aqueous solution, and the mixture was stirred at 80 C. for 2 hours. The resultant reaction liquid was cooled, then, dropped into methanol, to generate a precipitate. The resultant precipitate was collected by filtration, and washed with methanol and water, respectively, then, dried. The resultant solid was dissolved in chloroform, and purified by sequentially passing through an alumina column and a silica gel column through which chloroform had been passed previously. The resultant purified liquid was dropped into methanol, and the liquid was stirred, to generate a precipitate. The resultant precipitate was collected by filtration, and dried, to obtain a polymer compound ETL-1a (7.15 g). The polymer compound ETL-1a had an Mn of 3.210.sup.4 and an Mw of 6.010.sup.4.

[0378] The polymer compound ETL-1a is a copolymer constituted of a constitutional unit derived from the compound M4 and a constitutional unit derived from the compound M5 at a molar ratio of 50:50, according to the theoretical values calculated from the amounts of the charged raw materials.

[0379] An argon gas atmosphere was prepared in a reaction vessel, then, the polymer compound ETL-1a (3.1 g), tetrahydrofuran (130 mL), methanol (66 mL), cesium hydroxide monohydrate (2.1 g) and water (12.5 mL) were added, and the mixture was stirred at 60 C. for 3 hours. Thereafter, to this was added methanol (220 mL), and the mixture was stirred for 2 hours. The resultant reaction mixture was concentrated, then, dropped into isopropyl alcohol, and the liquid was stirred, to generate a precipitate. The resultant precipitate was collected by filtration, and dried, to obtain a polymer compound ETL-1 (3.5 g). By .sup.1H-NMR analysis of the polymer compound ETL-1, it was confirmed that a signal of an ethyl ester site in the polymer compound ETL-1 disappeared and reaction was completed.

[0380] The polymer compound ETL-1 is a copolymer constituted of a constitutional unit represented by the following formula and a constitutional unit derived from the compound M5 at a molar ratio of 50:50, according to the theoretical values calculated from the amounts of the charged raw materials of the polymer compound ETL-1a.

##STR00070##

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

(Formation of Anode and Hole Injection Layer)

[0381] An ITO film with a thickness of 45 nm was deposited on a glass substrate by a sputtering method, to form an anode. On the anode, a hole injection material ND-3202 (manufactured by Nissan Chemical Corporation) was spin-coated to form a film with a thickness of 35 nm. In an air atmosphere, the film was heated on a hot plate at 50 C. for 3 minutes, further heated at 230 C. for 15 minutes, to form a hole injection layer.

(Formation of Hole Transporting Layer)

[0382] The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. 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 60 minutes under a nitrogen gas atmosphere, to form a hole transporting layer.

(Formation of Light Emitting Layer)

[0383] The compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) were dissolved in toluene at a concentration of 2.0% by mass. The resultant toluene solution was spin-coated on the hole transporting layer, to form a film with a thickness of 75 nm, and the film was heated at 130 C. for 10 minutes under a nitrogen gas atmosphere, to form a light emitting layer.

(Formation of Electron Transporting Layer)

[0384] The polymer compound ETL-1 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. The resultant 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution was spin-coated on the light emitting layer, to form a film with a thickness of 10 nm, and the film was heated at 130 C. for 10 minutes under a nitrogen gas atmosphere, to form an electron transporting layer.

(Formation of Cathode)

[0385] The substrate carrying the electron transporting layer formed thereon was placed in a vapor deposition machine and the inner pressure thereof was reduced to 1.010.sup.4 Pa or less, then, as cathode, sodium fluoride was vapor-deposited with a thickness of about 4 nm on the electron transporting layer, then, aluminum was vapor-deposited with a thickness of about 80 nm on the sodium fluoride layer. After vapor deposition, sealing was performed with a glass substrate, to fabricate a light emitting device D1.

(Evaluation of Light Emitting Device)

[0386] Voltage was applied to the light emitting device D1, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.19, 0.41).

<Example D2> Fabrication and Evaluation of Light Emitting Device D2

[0387] A light emitting device D2 was fabricated in the same manner as in Example D1, except that the phosphorescent compound B2 was used instead of the phosphorescent compound B4 in (Formation of light emitting layer) in Example D1.

[0388] Voltage was applied to the light emitting device D2, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.16, 0.35).

<Example D3> Fabrication and Evaluation of Light Emitting Device D3

[0389] A light emitting device D3 was fabricated in the same manner as in Example D1, except that the phosphorescent compound B6 was used instead of the phosphorescent compound B4 in (Formation of light emitting layer) in Example D1.

[0390] Voltage was applied to the light emitting device D3, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.18, 0.36).

<Comparative Example CD1> Fabrication and Evaluation of Light Emitting Device CD1

[0391] A light emitting device CD1 was fabricated in the same manner as in Example D1, except that the phosphorescent compound B1 was used instead of the phosphorescent compound B4 in (Formation of light emitting layer) in Example D1.

[0392] Voltage was applied to the light emitting device CD1, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.16, 0.35).

[0393] The results of Examples D1 to D3 and Comparative Example CD1 are shown in Table 1. The relative values of the light emission efficiency of the light emitting devices D1 to D3 are shown when the light emission efficiency of the light emitting device CD1 is taken as 1.0.

TABLE-US-00001 TABLE 1 light emitting layer light emission light emitting hole transporting composition ratio efficiency device layer material material (% by mass) (relative value) Example D1 D1 HTL-1 HM-3/B4 75/25 64.3 Example D2 D2 HTL-1 HM-3/B2 75/25 30.3 Example D3 D3 HTL-1 HM-3/B6 75/25 37.1 Comparative CD1 HTL-1 HM-3/B1 75/25 1.0 Example CD1

<Example D4> Fabrication and Evaluation of Light Emitting Device D4

[0394] A light emitting device D4 was fabricated in the same manner as in Example D1, except that the compound HM-3, the compound HM-2 and the phosphorescent compound B2 (compound HM-3/compound HM-2/phosphorescent compound B2=37.5% by mass/37.5% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0395] Voltage was applied to the light emitting device D4, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.16, 0.36).

<Example D5> Fabrication and Evaluation of Light Emitting Device D5

[0396] A light emitting device D5 was fabricated in the same manner as in Example D4, except that the compound HM-4 was used instead of the compound HM-2 in (Formation of light emitting layer) in Example D4.

[0397] Voltage was applied to the light emitting device D5, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.17, 0.37).

<Example D6> Fabrication and Evaluation of Light Emitting Device D6

[0398] A light emitting device D6 was fabricated in the same manner as in Example D4, except that the phosphorescent compound B4 was used instead of the phosphorescent compound B2 in (Formation of light emitting layer) in Example D4.

[0399] Voltage was applied to the light emitting device D6, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.19, 0.39).

<Example D7> Fabrication and Evaluation of Light Emitting Device D7

[0400] A light emitting device D7 was fabricated in the same manner as in Example D4, except that the compound HM-3, the compound HM-1 and the phosphorescent compound B4 (compound HM-3/compound HM-1/phosphorescent compound B4=37.5% by mass/37.5% by mass/25% by mass) were used instead of the compound HM-3, the compound HM-2 and the phosphorescent compound B2 (compound HM-3/compound HM-2/phosphorescent compound B2=37.5% by mass/37.5% by mass/25% by mass) in (Formation of light emitting layer) in Example D4.

[0401] Voltage was applied to the light emitting device D7, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.17, 0.34).

<Example D8> Fabrication and Evaluation of Light Emitting Device D8

[0402] A light emitting device D8 was fabricated in the same manner as in Example D4, except that the phosphorescent compound B6 was used instead of the phosphorescent compound B2 in (Formation of light emitting layer) in Example D4.

[0403] Voltage was applied to the light emitting device D8, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.19, 0.38).

<Comparative Example CD2> Fabrication and Evaluation of Light Emitting Device CD2

[0404] A light emitting device CD2 was fabricated in the same manner as in Example D4, except that the phosphorescent compound B1 was used instead of the phosphorescent compound B2 in (Formation of light emitting layer) in Example D4.

[0405] Voltage was applied to the light emitting device CD2, to observe EL light emission. The light emission efficiency [cd/A] at 200 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 200 cd/m.sup.2 was (0.16, 0.35).

[0406] The results of Examples D4 to D8 and Comparative Example CD2 are shown in Table 2. The relative values of the light emission efficiency of the light emitting devices D4 to D8 are shown when the light emission efficiency of the light emitting device CD2 is taken as 1.0.

TABLE-US-00002 TABLE 2 light emitting layer light emission light emitting hole transporting composition ratio efficiency device layer material material (% by mass) (relative value) Example D4 D4 HTL-1 HM-3/HM-2/B2 37.5/37.5/25 12.9 Example D5 D5 HTL-1 HM-3/HM-4/B2 37.5/37.5/25 10.5 Example D6 D6 HTL-1 HM-3/HM-2/B4 37.5/37.5/25 22.4 Example D7 D7 HTL-1 HM-3/HM-1/B4 37.5/37.5/25 15.4 Example D8 D8 HTL-1 HM-3/HM-2/B6 37.5/37.5/25 15.5 Comparative CD2 HTL-1 HM-3/HM-2/B1 37.5/37.5/25 1.0 Example CD2

<Example D9> Fabrication and Evaluation of Light Emitting Device D9

[0407] A light emitting device D9 was fabricated in the same manner as in Example D1, except that the compound HM-4 was used instead of the compound HM-3 in (Formation of light emitting layer) in Example D1.

[0408] Voltage was applied to the light emitting device D9, to observe EL light emission. The light emission efficiency [cd/A] at 1000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 1000 cd/m.sup.2 was (0.19, 0.41).

<Example D10> Fabrication and Evaluation of Light Emitting Device D10

[0409] A light emitting device D10 was fabricated in the same manner as in Example D1, except that the compound HM-4 and the phosphorescent compound B5 (compound HM-4/phosphorescent compound B5=75% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0410] Voltage was applied to the light emitting device D10, to observe EL light emission. The light emission efficiency [cd/A] at 1000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 1000 cd/m.sup.2 was (0.19, 0.39).

<Example D11> Fabrication and Evaluation of Light Emitting Device D11

[0411] A light emitting device D1l was fabricated in the same manner as in Example D1, except that the compound HM-4 and the phosphorescent compound B2 (compound HM-4/phosphorescent compound B2=75% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0412] Voltage was applied to the light emitting device D11, to observe EL light emission. The light emission efficiency [cd/A] at 1000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 1000 cd/m.sup.2 was (0.16, 0.35).

<Example D12> Fabrication and Evaluation of Light Emitting Device D12

[0413] A light emitting device D12 was fabricated in the same manner as in Example D1, except that the compound HM-9 and the phosphorescent compound B4 (compound HM-9/phosphorescent compound B4=75% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0414] Voltage was applied to the light emitting device D12, to observe EL light emission. The light emission efficiency [cd/A] at 1000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 1000 cd/m.sup.2 was (0.19, 0.39).

<Comparative Example CD3> Fabrication and Evaluation of Light Emitting Device CD3

[0415] A light emitting device CD3 was fabricated in the same manner as in Example D1, except that the compound HM-1 and the phosphorescent compound B2 (compound HM-1/phosphorescent compound B2=75% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0416] Voltage was applied to the light emitting device CD3, to observe EL light emission. The light emission efficiency [cd/A] at 1000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 1000 cd/m.sup.2 was (0.17, 0.38).

<Comparative Example CD4> Fabrication and Evaluation of Light Emitting Device CD4

[0417] A light emitting device CD4 was fabricated in the same manner as in Example D1, except that the compound HM-4 and the phosphorescent compound B8 (compound HM-4/phosphorescent compound B8=75% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75: by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0418] Voltage was applied to the light emitting device CD4, to observe EL light emission. The light emission efficiency [cd/A] at 1000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 1000 cd/m.sup.2 was (0.20, 0.45).

[0419] The results of Examples D9 to D12 and Comparative Examples CD3 to CD4 are shown in Table 3. The relative values of the light emission efficiency of the light emitting devices D9 to D12 and CD4 are shown when the light emission efficiency of the light emitting device CD3 is taken as 1.00.

TABLE-US-00003 TABLE 3 light emitting layer light emission light emitting hole transporting composition ratio efficiency device layer material material (% by mass) (relative value) Example D9 D9 HTL-1 HM-4/B4 75/25 4.47 Example D10 D10 HTL-1 HM-4/B5 75/25 2.90 Example D11 D11 HTL-1 HM-4/B2 75/25 1.77 Example D12 D12 HTL-1 HM-9/B4 75/25 1.80 Comparative CD3 HTL-1 HM-1/B2 75/25 1.00 Example CD3 Comparative CD4 HTL-1 HM-4/B8 75/25 1.48 Example CD4

<Example D13> Fabrication and Evaluation of Light Emitting Device D13

(Formation of Anode and Hole Injection Layer)

[0420] An ITO film with a thickness of 45 nm was deposited on a glass substrate by a sputtering method, to form an anode. On the anode, a hole injection material ND-3202 (manufactured by Nissan Chemical Corporation) was spin-coated, to form a film with a thickness of 35 nm. In an air atmosphere, the film was heated on a hot plate at 50 C. for 3 minutes, further heated at 230 C. for 15 minutes, to form a hole injection layer.

(Formation of Second Light Emitting Layer)

[0421] The polymer compound HTL-2 was dissolved in xylene at a concentration of 0.7% by mass. 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 60 minutes under a nitrogen gas atmosphere, to form a second light emitting layer.

(Formation of First Light Emitting Layer)

[0422] The compound HM-2, the phosphorescent compound B3 and the phosphorescent compound G1 (compound HM-2/phosphorescent compound B3/phosphorescent compound G1=74% by mass/25% by mass/lx by mass) were dissolved in toluene at a concentration of 2.0% by mass. The resultant toluene solution was spin-coated on the second light emitting layer, to form a film with a thickness of 75 nm, and the film was heated at 130 C. for 10 minutes under a nitrogen gas atmosphere, to form a first light emitting layer.

(Formation of Electron Transporting Layer)

[0423] The polymer compound ETL-1 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25-. by mass. The resultant 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution was spin-coated on the first light emitting layer, to form a film with a thickness of 10 nm, and the film was heated at 130 C. for 10 minutes under a nitrogen gas atmosphere, to form an electron transporting layer.

(Formation of Cathode)

[0424] The substrate carrying the electron transporting layer formed thereon was placed in a vapor deposition machine and the inner pressure thereof was reduced to 1.010.sup.4 Pa or less, then, as cathode, sodium fluoride was vapor-deposited with a thickness of about 4 nm on the electron transporting layer, then, aluminum was vapor-deposited with a thickness of about 80 nm on the sodium fluoride layer. After vapor deposition, sealing was performed with a glass substrate, to fabricate a light emitting device D13.

(Evaluation of Light Emitting Device)

[0425] Voltage was applied to the light emitting device D13, to observe EL light emission. The light emission efficiency [cd/A] at 400 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 400 cd/m.sup.2 was (0.41, 0.46).

<Comparative Example CD5> Fabrication and Evaluation of Light Emitting Device CD5

[0426] A light emitting device CD5 was fabricated in the same manner as in Example D13, except that the compound HM-1 was used instead of the compound HM-2 in (Formation of first light emitting layer) in Example D13.

[0427] Voltage was applied to the light emitting device CD5, to observe EL light emission. The light emission efficiency [cd/A] at 400 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 400 cd/m.sup.2 was (0.40, 0.44).

[0428] The results of Example D13 and Comparative Example CD5 are shown in Table 4. The relative value of the light emission efficiency of the light emitting device D13 is shown when the light emission efficiency of the light emitting device D15 is taken as 1.00.

TABLE-US-00004 TABLE 4 first light second light emitting layer light emission light emitting emitting composition ratio efficiency device layer material material (% by mass) (relative value) Example D13 D13 HTL-2 HM-2/B3/G1 74/25/1 1.14 Comparative CD5 HTL-2 HM-1/B3/G1 74/25/1 1.00 Example CD5

<Example D14> Fabrication and Evaluation of Light Emitting Device D14

[0429] A light emitting device D14 was fabricated in the same manner as in Example D13, except that the compound HM-3, the phosphorescent compound B7 and the phosphorescent compound G1 (compound HM-3/phosphorescent compound B7/phosphorescent compound G1=74% by mass/25% by mass/1% by mass) were used instead of the compound HM-2, the phosphorescent compound B3 and the phosphorescent compound G1 (compound HM-2/phosphorescent compound B3/phosphorescent compound G1=74% by mass/25% by mass/1% by mass) in (Formation of first light emitting layer) in Example D13.

[0430] Voltage was applied to the light emitting device D14, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.45, 0.46).

<Example D15> Fabrication and Evaluation of Light Emitting Device D15

[0431] A light emitting device D15 was fabricated in the same manner as in Example D14, except that the compound HM-2 was used instead of the compound HM-3 in (Formation of first light emitting layer) in Example D14.

[0432] Voltage was applied to the light emitting device D15, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.47, 0.45).

<Example D16> Fabrication and Evaluation of Light Emitting Device D16

[0433] A light emitting device D16 was fabricated in the same manner as in Example D14, except that the compound HM-8 was used instead of the compound HM-3 in (Formation of first light emitting layer) in Example D14.

[0434] Voltage was applied to the light emitting device D16, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.48, 0.45).

<Example D17> Fabrication and Evaluation of Light Emitting Device D17

[0435] A light emitting device D17 was fabricated in the same manner as in Example D14, except that the compound HM-5 was used instead of the compound HM-3 in (Formation of first light emitting layer) in Example D14.

[0436] Voltage was applied to the light emitting device D17, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.43, 0.46).

<Comparative Example CD6> Fabrication and Evaluation of Light Emitting Device CD6

[0437] A light emitting device CD6 was fabricated in the same manner as in Example D14, except that the compound HM-1 was used instead of the compound HM-3 in (Formation of first light emitting layer) in Example D14.

[0438] Voltage was applied to the light emitting device CD6, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.48, 0.45).

<Comparative Example CD7> Fabrication and Evaluation of Light Emitting Device CD7

[0439] A light emitting device CD7 was fabricated in the same manner as in Example D13, except that the compound HM-2, the phosphorescent compound B8 and the phosphorescent compound G1 (compound HM-2/phosphorescent compound B8/phosphorescent compound G1=74% by mass/25% by mass/l % by mass) were used instead of the compound HM-2, the phosphorescent compound B3 and the phosphorescent compound G1 (compound HM-2/phosphorescent compound B3/phosphorescent compound G1=74% by mass/25: by mass/1% by mass) in (Formation of first light emitting layer) in Example D13.

[0440] Voltage was applied to the light emitting device CD7, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.47, 0.46).

[0441] The results of Examples D14 to D17 and Comparative Examples CD6 to CD7 are shown in Table 5. The relative values of the light emission efficiency of the light emitting devices D14 to D17 and CD7 are shown when the light emission efficiency of the light emitting device CD6 is taken as 1.00.

TABLE-US-00005 TABLE 5 first light second light emitting layer light emission light emitting emitting composition ratio efficiency device layer material material (% by mass) (relative value) Example D14 D14 HTL-2 HM-3/B7/G1 74/25/1 1.19 Example D15 D15 HTL-2 HM-2/B7/G1 74/25/1 1.17 Example D16 D16 HTL-2 HM-8/B7/G1 74/25/1 1.16 Example D17 D17 HTL-2 HM-5/B7/G1 74/25/1 1.29 Comparative CD6 HTL-2 HM-1/B7/G1 74/25/1 1.00 Example CD6 Comparative CD7 HTL-2 HM-2/B8/G1 74/25/1 0.92 Example CD7

<Example D18> Fabrication and Evaluation of Light Emitting Device D18

[0442] A light emitting device D18 was fabricated in the same manner as in Example D1, except that the compound HM-2, the phosphorescent compound B2, the phosphorescent compound G2 and the phosphorescent compound R1 (compound HM-2/phosphorescent compound B2/phosphorescent compound G2/phosphorescent compound R1=62.05% by mass/37.5% by mass/0.25% by mass/0.20% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0443] Voltage was applied to the light emitting device D18, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.34, 0.41).

<Comparative Example CD8> Fabrication and Evaluation of Light Emitting Device CD8

[0444] A light emitting device CD8 was fabricated in the same manner as in Example D1, except that the compound HM-1, the phosphorescent compound B2, the phosphorescent compound G2 and the phosphorescent compound R1 (compound HM-1/phosphorescent compound B2/phosphorescent compound G2/phosphorescent compound R1=62.05% by mass/37.5% by mass/0.25% by mass/0.20% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25% by mass) in (Formation of light emitting layer) in Example D1.

[0445] Voltage was applied to the light emitting device CD8, to observe EL light emission. The light emission efficiency [cd/A] at 10000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 10000 cd/m.sup.2 was (0.31, 0.38).

[0446] The results of Example D18 and Comparative Example CD8 are shown in Table 6. The relative value of the light emission efficiency of the light emitting device D18 is shown when the light emission efficiency of the light emitting device CD8 is taken as 1.00.

TABLE-US-00006 TABLE 6 light emitting layer light emission light emitting hole transporting composition ratio efficiency device layer materia1 material (% by mass) (relative value) Example D17 D17 HTL-1 HM-2/B2/G2/R1 62.05/37.5/0.25/0.20 1.18 Comparative CD8 HTL-1 HM-1/B2/G2/R1 62.05/37.5/0.25/0.20 1.00 Example CD8

<Example D19> Fabrication and Evaluation of Light Emitting Device D19

[0447] A light emitting device D19 was fabricated in the same manner as in Example D1, except that the compound HM-3 and the phosphorescent compound B7 (compound HM-3/phosphorescent compound B7=75% by mass/25% by mass) were used instead of the compound HM-3 and the phosphorescent compound B4 (compound HM-3/phosphorescent compound B4=75% by mass/25-. by mass) in (Formation of light emitting layer) in Example D1.

[0448] Voltage was applied to the light emitting device D19, to observe EL light emission. The light emission efficiency [cd/A] at 5000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 5000 cd/m.sup.2 was (0.20, 0.44).

<Example D20> Fabrication and Evaluation of Light Emitting Device D20

[0449] A light emitting device D20 was fabricated in the same manner as in Example D19, except that the compound HM-2 was used instead of the compound HM-3 in (Formation of light emitting layer) in Example D19.

[0450] Voltage was applied to the light emitting device D20, to observe EL light emission. The light emission efficiency [cd/A] at 5000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 5000 cd/m.sup.2 was (0.21, 0.46).

<Example D21> Fabrication and Evaluation of Light Emitting Device D21

[0451] A light emitting device D21 was fabricated in the same manner as in Example D19, except that the compound HM-8 was used instead of the compound HM-3 in (Formation of light emitting layer) in Example D19.

[0452] Voltage was applied to the light emitting device D21, to observe EL light emission. The light emission efficiency [cd/A] at 5000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 5000 cd/m.sup.2 was (0.20, 0.44).

<Example D22> Fabrication and Evaluation of Light Emitting Device D22

[0453] A light emitting device D22 was fabricated in the same manner as in Example D19, except that the compound HM-5 was used instead of the compound HM-3 in (Formation of light emitting layer) in Example D19.

[0454] Voltage was applied to the light emitting device D22, to observe EL light emission. The light emission efficiency [cd/A] at 5000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 5000 cd/m.sup.2 was (0.19, 0.41).

<Example D23> Fabrication and Evaluation of Light Emitting Device D23

[0455] A light emitting device D23 was fabricated in the same manner as in Example D19, except that the compound HM-7 was used instead of the compound HM-3 in (Formation of light emitting layer) in Example D19.

[0456] Voltage was applied to the light emitting device D23, to observe EL light emission. The light emission efficiency [cd/A] at 5000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 5000 cd/m.sup.2 was (0.21, 0.46).

<Example D24> Fabrication and Evaluation of Light Emitting Device D24

[0457] A light emitting device D24 was fabricated in the same manner as in Example D19, except that the compound HM-6 was used instead of the compound HM-3 in (Formation of light emitting layer) in Example D19.

[0458] Voltage was applied to the light emitting device D24, to observe EL light emission. The light emission efficiency [cd/A] at 5000 cd/m.sup.2 was measured. The CIE chromaticity coordinate (x, y) at 5000 cd/m.sup.2 was (0.22, 0.47).

[0459] The results of Examples D19 to D24 are shown in Table 7. The relative values of the light emission efficiency of the light emitting devices D19 to D23 are shown when the light emission efficiency of the light emitting device D24 is taken as 1.00.

TABLE-US-00007 TABLE 7 light emitting layer light emission light emitting hole transporting composition ratio efficiency device layer material material (% by mass) (relative value) Example D19 D19 HTL-1 HM-3/B7 75/25 2.04 Example D20 D20 HTL-1 HM-2/B7 75/25 1.43 Example D21 D21 HTL-1 HM-8/B7 75/25 1.42 Example D22 D22 HTL-1 HM-5/B7 75/25 1.43 Example D23 D23 HTL-1 HM-7/B7 75/25 1.27 Example D24 D24 HTL-1 HM-6/B7 75/25 1.00

INDUSTRIAL APPLICABILITY

[0460] According to the present invention, a composition which is useful for production of a light emitting device excellent in light emission efficiency can be provided. Further, according to the present invention, a light emitting device comprising this composition can be provided.