Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic apparatus

Abstract

A compound represented by formula (1): ##STR00001##
wherein Ar.sup.1 and Ar.sup.2 each represents a group represented by formula (3); ##STR00002##
and R.sup.1 represents a naphthylphenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, or a phenylnaphthyl group; R.sup.2 represents a hydrogen atom; R.sup.5 and R.sup.6 are as defined in the description is provided. An electroluminescence device which contains the compound of formula (1) is also provided.

Claims

1. A compound represented by formula (1), ##STR00110## wherein: R.sup.1 represents a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, or a phenylnaphthyl group; the aryl group and a benzene ring to which R.sup.1 is bonded may be crosslinked; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 represents a group represented by formula (3): ##STR00111## wherein: R.sup.5 and R.sup.6 each independently represent an unsubstituted alkyl group having 1 to 20 carbon atoms, L.sup.2 represents a substituted or unsubstituted arylene group having 6 to 50 ring carton atoms; z represents 0 and (L.sup.2).sub.0 represents a single bond; R.sup.4 represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; n represents an integer of 0 to 4, when n is an integer of 2 to 4, two to four groups R.sup.4 may be the same or different and may be bonded to each other to form a ring, and when n is 0, (R.sup.4).sub.0 represents a hydrogen atom.

2. The compound according to claim 1, wherein the group of formula (1) represented by formula (4): ##STR00112## is represented by formula (4a): ##STR00113## wherein R.sup.1 is as defined in formula (1).

3. The compound according to claim 1, wherein formula (3) is represented by formula (3a′): ##STR00114## wherein R.sup.4, R.sup.5, R.sup.6, and n are as defined in formula (1).

4. The compound according to claim 1, wherein formula (3) is represented by formula (3a″): ##STR00115## wherein R.sup.5 and R.sup.6 are as defined in formula (1).

5. The compound according to claim 1, wherein formula (1) is represented by formula (1a): ##STR00116## wherein R.sup.1, Ar.sup.2 and Ar.sup.2 are as defined in formula (1).

6. The compound according to claim 1, wherein formula (1) is represented by formulae (1a-3): ##STR00117## wherein Ar.sup.2 represents a group represented by formula (3a′): ##STR00118##   and R.sup.1, R.sup.4, R.sup.5, R.sup.6, and n are as defined in formula 1).

7. The compound according to claim 1, wherein formula (1) is represented by formula (1a-3′): ##STR00119## wherein Ar.sup.2 represents a group represented by formula (3a″): ##STR00120##   and R.sup.1, R.sup.5, and R.sup.6 are as defined in formula (1).

8. The compound according to claim 1, wherein R.sup.5 and R.sup.6 each independently represent a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group.

9. The compound according to claim 1, wherein R.sup.5 and R.sup.6 each independently represent a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, or a pentyl group.

10. The compound according to claim 1, wherein R.sup.5 and R.sup.6 each independently represent a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, or a t-butyl group.

11. The compound according to claim 1, wherein R.sup.5 and R.sup.6 each independently represent a methyl group or a t-butyl group.

12. The compound according to claim 1, wherein R.sup.5 and R.sup.6 both represent methyl groups.

13. The compound according to claim 1, wherein R.sup.1 represents a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, or a phenylnaphthyl group; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 each independently represent a group represented by formula (3a′) ##STR00121## wherein: R.sup.4 represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R.sup.5 and R.sup.6 each independently represent a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, or a t-butyl group; and n represents an integer of 0 to 4, when n is an integer of 2 to 4, two to four groups R.sup.4 may be the same or different and may be bonded to each other to form a ring, and when n is 0, (R.sup.4).sub.0 represents a hydrogen atom.

14. The compound according to claim 1, wherein R.sup.1 represents a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, or a phenylnaphthyl group; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 each independently represent a group represented by formula (3a′): ##STR00122## wherein: R.sup.4 represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R.sup.5 and R.sup.6 each independently represent a methyl group or a t-butyl group; and n represents an integer of 0 to 4, when n is an integer of 2 to 4, two to four groups R.sup.4 may be the same or different and may be bonded to each other to form a ring, and when n is 0, (R.sup.4).sub.0 represents a hydrogen atom.

15. The compound according to claim 1, wherein R.sup.1 represents a biphenylyl group; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 each independently represent a group represented by formula (3a′): ##STR00123## wherein: R.sup.4 represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R.sup.5 and R.sup.6 both represent methyl groups; and n represents an integer of 0 to 4, when n is an integer of 2 to 4, two to four groups R.sup.4 may be the same or different and may be bonded to each other to form a ring, and when n is 0, (R.sup.4).sub.0 represents a hydrogen atom.

16. The compound according to claim 1, wherein R.sup.1 represents a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, or a phenylnaphthyl group; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 each independently represent a group represented by formula (3a″): ##STR00124## wherein: R.sup.5 and R.sup.6 each independently represent a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, or a t-butyl group.

17. The compound according to claim 1, wherein R.sup.1 represents a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, or a phenylnaphthyl group; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 each independently represent a group represented by formula (3a′ ##STR00125## wherein: R.sup.5 and R.sup.6 each independently represent a methyl group or a t-butyl group.

18. The compound according to claim 1, wherein R.sup.1 represents a biphenylyl group; R.sup.2 represents a hydrogen atom; Ar.sup.1 and Ar.sup.2 each independently represent a group represented by formula (3a”): ##STR00126## wherein: R.sup.5 and R.sup.6 both represent methyl groups.

19. A material for organic electroluminescence devices which comprises the compound according to claim 1.

20. An organic electroluminescence device which comprises an anode, a cathode, and at least one organic thin film layer between the anode and the cathode, wherein: the at least one organic thin film layer comprises a light emitting layer; and at least one layer of the at least one organic thin film layer comprises the compound according to claim 1.

21. The organic electroluminescence device according to claim 20, wherein the organic electroluminescence device comprises an organic thin film layer between the anode and the light emitting layer and the organic thin film layer comprises the compound.

22. The organic electroluminescence device according to claim 21, wherein: the organic thin film layer comprises a hole injecting layer and a hole transporting layer; and the hole injecting layer or the hole transporting layer comprises the aromatic amine derivative.

23. The organic electroluminescence device according to claim 20, wherein: the at least one organic thin film layer comprises a hole transporting layer between the anode and the light emitting layer; the hole transporting layer comprises a first hole transporting layer at an anode side and a second hole transporting layer at a cathode side; and any of the first hole transporting layer and the second hole transporting layer comprises the aromatic amine derivative.

24. The organic electroluminescence device according to claim 23, wherein the first hole transporting layer comprises the aromatic amine derivative.

25. The organic electroluminescence device according to claim 23, wherein the second hole transporting layer comprises the aromatic amine derivative.

26. The organic electroluminescence device according to claim 20, wherein: the at least one organic thin film layer between the anode and the light emitting layer consists of in the order of listed: a hole injecting layer, a first hole transporting layer at an anode side, and a second hole transporting layer at a cathode side, wherein any of the first hole transporting layer and the second hole transporting layer comprises the aromatic amine derivative.

27. The organic electroluminescence device according to claim 20, comprising, in the order listed: the anode; a hole injecting layer; a hole transporting layer that consists of a first hole transporting layer at an anode side and a second hole transporting layer at a cathode side; the light emitting layer; and the cathode; wherein any of the first hole transporting layer and the second hole transporting layer comprises the aromatic amine derivative.

28. The organic electroluminescence device according to claim 27, wherein the first hole transporting layer comprises the aromatic amine derivative.

29. The organic electroluminescence device according to claim 27, wherein the second hole transporting layer comprises the aromatic amine derivative.

30. An electronic equipment which comprises the organic electroluminescence device according to claim 20.

Description

EXAMPLES

(1) The present invention will be descried below in more detail with reference to the examples. However, it should be noted that the scope of the present invention is not limited thereto.

(2) Intermediate Synthesis 1-1; Synthesis of Intermediate 1-1

(3) Under an argon atmosphere, into a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of Pd[PPh.sub.3].sub.4, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na.sub.2CO.sub.3 were added. The obtained mixture was refluxed for 10 h under heating and stirring.

(4) After the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane in a separating funnel. The organic layer was dried over MgSO.sub.4, filtered, and then concentrated. The residual concentrate was purified by silica gel column chromatography to obtain 26.2 g of a white solid, which was identified by FD-MS analysis (field desorption mass spectrometry) as the following intermediate 1-1 (yield: 81%).

(5) ##STR00090##
Intermediate Synthesis 1-2: Synthesis of intermediate 1-2

(6) Under a nitrogen atmosphere, 150 g (0.89 mol) of dibenzofuran was dissolved in 1000 ml of acetic acid under heating. After further adding 188 g (1.18 mol) of bromine dropwise, the resultant solution was stirred at room temperature for 20 h. The precipitated crystal was collected by filtration and successively washed with acetic acid and water. The obtained crude product was recrystallized from methanol several times to obtain 66.8 g of a white crystal, which was identified by FD-MS analysis as the following intermediate 1-2 (yield: 30%).

(7) ##STR00091##
Intermediate Synthesis 1-3: Synthesis of intermediate 1-3

(8) Under an argon atmosphere, a solution of 24.7 g (100.0 mmol) of the intermediate 1-2 in 400 ml of dehydrated tetrahydrofuran was cooled to −40° C., and then 63 ml (100.0 mmol) of a 1.6 M hexane solution of n-butyllithium was gradually added. After stirring for one hour under heating to 0° C., the reaction solution was again cooled to −78° C. and a solution of 26.0 g (250.0 mmol) of trimethyl borate in 50 ml of dehydrated tetrahydrofuran was added dropwise. After the addition, the reaction solution was stirred at room temperature for 5 h. After adding 200 ml of a 1 N hydrochloric acid, the solution was stirred for one hour and then the aqueous layer was removed. The organic layer was dried over MgSO.sub.4 and the solvent was evaporated off under reduced pressure. The obtained solid was washed with toluene to obtain 15.2 g of a white crystal, which was identified by FD-MS analysis as the following intermediate 1-3 (yield: 72%).

(9) ##STR00092##
Intermediate Synthesis 1-4: Synthesis of intermediate 1-4

(10) Under an argon atmosphere, into a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of the intermediate 1-3, and 2.31 g (2.00 mmol) of Pd[PPh.sub.3].sub.4, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na.sub.2CO.sub.3 were added. The obtained mixture was refluxed for 10 h under heating and stirring.

(11) After the reaction, the reaction mixture was extracted with dichloromethane in a separating funnel. The organic layer was dried over MgSO.sub.4, filtered, and then concentrated. The residual concentrate was purified by silica gel column chromatography to obtain 24.2 g of a white solid, which was identified by FD-MS analysis as the following intermediate 1-4 (yield: 75%).

(12) ##STR00093##
Intermediate Synthesis 1-5: Synthesis of intermediate 1-5

(13) Under an argon atmosphere, into a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 23.9 g (105.0 mmol) of dibenzothiophene-4-boronic acid, and 2.31 g (2.00 mmol) of Pd[PPh.sub.3].sub.4, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na.sub.2CO.sub.3 were added. The obtained mixture was refluxed for 10 h under heating and stirring.

(14) After the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane in a separating funnel. The organic layer was dried over MgSO.sub.4, filtered, and then concentrated. The residual concentrate was purified by silica gel column chromatography to obtain 27.1 g of a white solid, which was identified by FD-MS analysis as the following intermediate 1-5 (yield: 80%).

(15) ##STR00094##
Intermediate Synthesis 2-1: Synthesis of intermediate 2-1

(16) Under an argon atmosphere, into a mixture of 19.9 g (50.0 mmol) of 2-bromo-9,9′-diphenylfluorene, 12.3 g (50.0 mmol) of [1,1′:4′,1″]terphenyl-2-ylamine, and 9.6 g (100.0 mmol) of sodium t-butoxide, 250 ml of dehydrated toluene was added, and the resultant mixture was stirred. After adding 225 mg (1.0 mmol) of palladium acetate and 202 mg (1.0 mmol) of tri-t-butylphosphine, the mixture was allowed to react at 80° C. for 8 h.

(17) After cooling, the reaction mixture was filtered through celite/silica gel, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from toluene, and the crystal collected by filtration was dried to obtain 19.7 g of a white solid, which was identified by FD-MS analysis as the following intermediate 2-1 (yield: 70%).

(18) ##STR00095##
Intermediate Synthesis 2-2: Synthesis of intermediate 2-2

(19) In the same manner as in Intermediate Synthesis 2-1 except for using [1,1′:3′,1″]terphenyl-2-ylamine in place of [1,1′:4′,1″]terphenyl-2-ylamine, 21.1 g of a white solid was obtained, which was identified by FD-MS analysis as the following intermediate 2-2 (yield: 75%).

(20) ##STR00096##
Intermediate Synthesis 2-3: Synthesis of intermediate 2-3

(21) In the same manner as in Intermediate Synthesis 2-1 except for using [1,1′:4′,1″]terphenyl-3′-ylamine in place of [1,1′:4′,1″]terphenyl-2-ylamine, 19.7 g of a white solid was obtained, which was identified by FD-MS analysis as the following intermediate 2-3 (yield: 70%).

(22) ##STR00097##

Synthesis Example 1

Production of Compound (H1)

(23) Under an argon atmosphere, into a mixture of 2.5 g (10.0 mmol) of the intermediate 1-2, 5.6 g (10.0 mmol) of the intermediate 2-1, 0.14 g (0.15 mmol) of Pd.sub.2(dba).sub.3, 0.087 g (0.3 mmol) of P(tBu).sub.3HBF.sub.4, and 1.9 g (20.0 mmol) of sodium t-butoxide, 50 ml of dehydrated xylene was added. The resultant mixture was refluxed for 8 h under heating.

(24) After the reaction, the reaction mixture was cooled to 50° C., filtered through celite/silica gel, and the filtrate was concentrated. The residual concentrate was purified by silica gel column chromatography to obtain a white solid. The crude product was recrystallized from toluene to obtain 3.6 g of a white crystal, which was identified by FD-MS analysis as the following compound (H1) (yield: 50%).

(25) ##STR00098##

Synthesis Example 2

Production of Compound (H2)

(26) In the same manner as in Synthesis Example 1 except for using 3.2 g of the intermediate 1-4 in place of the intermediate 1-2, 5.1 g of a white crystal was obtained, which was identified by FD-MS analysis as the following compound (H2) (yield: 63%).

(27) ##STR00099##

Synthesis Example 3

Production of Compound (H3)

(28) In the same manner as in Synthesis Example 1 except for using 3.4 g of the intermediate 1-5 in place of the intermediate 1-2, 4.1 g of a white crystal was obtained, which was identified by FD-MS analysis as the following compound (H3) (yield: 50%).

(29) ##STR00100##

Synthesis Example 4

Production of Compound (H4)

(30) In the same manner as in Synthesis Example 1 except for using 3.2 g of the intermediate 1-1 in place of the intermediate 1-2 and using 5.6 g of the intermediate 2-2 in place of the intermediate 2-1, 4.4 g of a white crystal was obtained, which was identified by FD-MS analysis as the following compound (H4) (yield: 55%).

(31) ##STR00101##

Synthesis Example 5

Production of Compound (H5)

(32) In the same manner as in Synthesis Example 1 except for using 3.2 g of the intermediate 1-1 in place of the intermediate 1-2 and using 5.6 g of the intermediate 2-3 in place of the intermediate 2-1, 4.4 g of a white crystal was obtained, which was identified by FD-MS analysis as the following compound (H5) (yield: 55%).

(33) ##STR00102##

Synthesis Example 6

Production of Compound (H6)

(34) In the same manner as in Synthesis Example 1 except for using 3.2 g of the intermediate 1-1 in place of the intermediate 1-2 and using 1.2 g of [1,1′:4′,1″]terphenyl-2-ylamine in place of the intermediate 2-1, 1.8 g of a white crystal was obtained, which was identified by FD-MS analysis as the following compound (H6) (yield: 50%).

(35) ##STR00103##

Example 1-1

Production of Organic EL Device

(36) A glass substrate of 25 mm×75 mm×1.1 mm having an ITO transparent electrode (product of Geomatec Company) was cleaned by ultrasonic cleaning in isopropyl alcohol for 5 min and then UV (ultraviolet) ozone cleaning for 30 min.

(37) The cleaned glass substrate having a transparent electrode line was mounted to a substrate holder of a vacuum vapor deposition apparatus. First, the following acceptor material (A) was vapor-deposited so as to cover the transparent electrode to form an acceptor layer with a thickness of 5 nm.

(38) On the acceptor layer, the following aromatic amine compound (HT1) as a first hole transporting material was vapor-deposited to form a first hole transporting layer with a thickness of 160 nm. Successively after forming the first hole transporting layer, the compound (H1) as a second hole transporting material was vapor-deposited to form a second hole transporting layer with a thickness of 10 nm.

(39) On the second hole transporting layer, the following host material and the following dopant as fluorescent emitting materials were vapor co-deposited to form a fluorescent emitting layer with a thickness of 25 nm. The concentration of the dopant in the fluorescent emitting layer was 4% by mass.

(40) Thereafter, on the fluorescent emitting layer, the following compound ET1, compound ET2, and Li were vapor co-deposited into a thickness of 20 nm, 10 nm, and 25 nm, respectively to form an electron transporting/injecting layer. The concentration of Li was 4% by weight. Further, metallic Al was deposited into a thickness of 80 nm to form a cathode, thereby producing an organic EL device.

(41) ##STR00104## ##STR00105##

Examples 1-2 to 1-6

(42) Each organic EL device of Examples 1-2 to 1-6 was produced in the same manner as in Example 1-1 except for forming the second hole transporting layer by using each compound shown in Table 1 as the second hole transporting material.

Comparative Examples 1 and 2

(43) Each organic EL device of Comparative Examples 1 and 2 was produced in the same manner as in Example 1-1 except for forming the second hole transporting layer by using the following comparative compound 1 (Comparative Example 1) or the following comparative compound 2 (Comparative Example 2) as the second hole transporting material.

(44) ##STR00106##
Evaluation of Emission Performance of Organic EL Device

(45) Each organic EL device thus produced was allowed to emit light by driving at a constant current to measure the luminance (L) and the current density. From the measured results, the emission efficiency (cd/A) and the driving voltage (V) at a current density of 10 mA/cm.sup.2 were determined. In addition, the 80% lifetime was measured. The 80% lifetime is the time taken until the luminance is reduced to 80% of the initial luminance when driving at a constant current. The results are shown in Table 1.

(46) TABLE-US-00001 TABLE 1 Second hole 80% lifetime transporting layer cd/A V (h) Example 1-1 H1 6.4 4.3 200 Example 1-2 H2 7.2 4.1 210 Example 1-3 H3 6.9 4.2 240 Example 1-4 H4 6.8 4.2 230 Example 1-5 H5 6.8 4.3 200 Example 1-6 H6 6.9 4.0 220 Comparative Comparative 5.5 4.2 120 example 1 compound 1 Comparative Comparative 1.5 5.0 80 example 2 compound 2

(47) As seen from Table 1, it can be found that an organic EL device having high efficiency even when driving at a low voltage and long lifetime is obtained by using each of the compounds (H1) to (H6) within formula (1).

Example 2-1

Production of Organic EL Device

(48) A glass substrate of 25 mm×75 mm×1.1 mm having an ITO transparent electrode (product of Geomatec Company) was cleaned by ultrasonic cleaning in isopropyl alcohol for 5 min and then UV (ultraviolet) ozone cleaning for 30 min.

(49) The cleaned glass substrate having a transparent electrode line was mounted to a substrate holder of a vacuum vapor deposition apparatus. First, the following acceptor material (A) was vapor-deposited so as to cover the transparent electrode to form an acceptor layer with a thickness of 5 nm.

(50) On the acceptor layer, the compound (H2) as a first hole transporting material was vapor-deposited to form a first hole transporting layer with a thickness of 160 nm. Successively after forming the first hole transporting layer, the following aromatic amine derivative (Y1) as a second hole transporting material was vapor-deposited to form a second hole transporting layer with a thickness of 10 nm.

(51) On the second hole transporting layer, the following host material and the following dopant as fluorescent emitting materials were vapor co-deposited to form a fluorescent emitting layer with a thickness of 25 nm. The concentration of the dopant in the fluorescent emitting layer was 4% by mass.

(52) Thereafter, on the fluorescent emitting layer, the following compound ET1, compound ET2, and Li were vapor co-deposited into a thickness of 20 nm, 10 nm, and 25 nm, respectively to form an electron transporting/injecting layer. The concentration of Li was 4% by weight. Further, metallic Al was deposited into a thickness of 80 nm to form a cathode, thereby producing an organic EL device.

(53) ##STR00107## ##STR00108##

Examples 2-2 and 2-3

(54) Each organic EL device of Examples 2-2 and 2-3 was produced in the same manner as in Example 2-1 except for forming the first hole transporting layer by using each compound shown in Table 2 as the first hole transporting material.

Comparative Example 3

(55) The organic EL device of Comparative Example 3 was produced in the same manner as in Example 2-1 except for forming the first hole transporting layer by using the following comparative compound 3 as the first hole transporting material.

(56) ##STR00109##
Evaluation of Emission Performance of Organic EL Device

(57) Each organic EL device thus produced was measured for the emission efficiency (cd/A) and the driving voltage (V) at a current density of 10 mA/cm.sup.2, and the 80% lifetime in the same manner as described above. The results are shown in Table 2.

(58) TABLE-US-00002 TABLE 2 First hole 80% lifetime transporting layer cd/A V (h) Example 2-1 H2 8.5 4.0 180 Example 2-2 H3 8.3 4.0 200 Example 2-3 H6 8.5 4.0 240 Comparative Comparative 7.2 4.0 110 example 3 compound 3

(59) As seen from Table 2, it can be found that an organic EL device having high efficiency even when driving at a low voltage and long lifetime is obtained by using each of the compounds (H2), (H3), and (H6) within formula (1).