ORGANIC MATERIAL COMPOSITION AND APPLICATIONS THEREOF

Abstract

The present invention provides an organic material composition and applications thereof. By the combination of the compounds comprised in the organic material composition, the organic material composition makes the element have a lower driving voltage, a higher current efficiency and a longer service life.

Claims

1. An organic material composition, characterized in that the organic material composition comprises at least one compound having a structure represented by Formula (1) and at least one compound having a structure represented by Formula (2): ##STR00141## wherein, R is selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R.sup.1 is -L.sup.1Ar.sup.1; R.sup.2 is -L.sup.2Ar.sup.2; R.sup.3 is -L.sup.3Ar.sup.3; R.sup.4 is -L.sup.4Ar.sup.4; L.sup.1 to L.sup.4 are each independently selected from a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar.sup.1 to Ar.sup.4 are each independently selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; ##STR00142## wherein, R′ is selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; L.sup.5 to L.sup.8 are each independently selected from a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar.sup.5 to Ar.sup.8 are each independently selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group.

2. The organic material composition according to claim 1, characterized in that, in Formula (1), at least one of Ar.sup.1 to Ar.sup.4 is a group represented by Formula (a): ##STR00143## wherein the wavy line represents the connection position of the group; X.sup.1 is selected from N and CR.sup.X1; X.sup.2 is selected from N and CR.sup.X2; X.sup.3 is selected from N and CR.sup.X3; X.sup.4 is selected from N and CR.sup.X4; X.sup.5 is selected from N and CR.sup.X5; R.sup.X1 to R.sup.X5 are each independently selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R.sup.X1-R.sup.X5 are present individually without forming a ring, or any adjacent two of R.sup.X1-R.sup.X5 joined to form a ring, and the ring is a benzene ring.

3. The organic material composition according to claim 2, characterized in that, R.sup.X1 to R.sup.X5 are each independently selected from hydrogen, deuterium, halogen, and a group selected from a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, an anthryl group, a phenylnaphthyl group, a naphthylphenyl group, a pyridyl group, a bipyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, a carbazolyl group, a carbazolylphenyl group, a phenylcarbazolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a dibenzofurylphenyl group, a dibenzothiophenylphenyl group, a dimethylfluorenylphenyl group, a benzocarbazolyl group, a benzonaphthofuryl group, and a benzonaphthothiophenyl group, each of which is substituted or unsubstituted; and in X.sup.1 to X.sup.5, X.sup.1 is N; X.sup.2 is N; X.sup.3 is CR.sup.X3; X.sup.4 is CR.sup.X4; and X.sup.5 is CR.sup.X5; or X.sup.1 is N; X.sup.3 is N; X.sup.2 is CR.sup.X2; X.sup.4 is CR.sup.X4; and X.sup.5 is CR.sup.X5; or X.sup.1 is N; X.sup.2 is N; X.sup.3 is N; X.sup.4 is CR.sup.X4; and X.sup.5 is CR.sup.X5; and L.sup.1 to L.sup.4 are each independently selected from a bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

4. The organic material composition according to claim 1, characterized in that the compound having a structure represented by Formula (1) is any one of the following compounds M1 to M206: ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## wherein D represents deuterium.

5. The organic material composition according to claim 1, characterized in that, in Formula (2), at least one of Ar.sup.5 to Ar.sup.8 is ##STR00213## wherein Ar.sup.9 and Ar.sup.10 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.

6. The organic material composition according to claim 1, characterized in that, the substituent is selected from deuterium, halogen, a cyano group, a nitro group, an unsubstituted or R″-substituted C1-C4 straight or branched alkyl group, an unsubstituted or R″-substituted C6-C20 aryl group, an unsubstituted or R″-substituted C3-C20 heteroaryl group, and an unsubstituted or R″-substituted C6-C20 arylamino group; R″ is selected from deuterium, halogen, a cyano group and a nitro group.

7. The organic material composition according to claim 1, characterized in that the compound having a structure represented by Formula (2) is any one of the following compounds N1 to N60: ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## and the compound having a structure represented by Formula (1) and the compound having a structure represented by Formula (2) have a weight ratio of 1:9 to 9:1.

8. The organic material composition according to claim 7, characterized in that the compound having a structure represented by Formula (1) and the compound having a structure represented by Formula (2) have a weight ratio of 4:6 to 6:4.

9. An organic electroluminescence material, characterized in that the organic electroluminescence material comprises the organic material composition according to claim 1.

10. An application of the organic material composition according to claim 1 in preparation of an optical element.

11. An organic electroluminescence element, characterized in that the organic electroluminescence element comprises an anode, a cathode and an organic layer disposed between the anode and the cathode; and the organic layer comprises the organic material composition according to claim 1.

12. An electronic device, characterized in that the electronic device comprises the organic electroluminescence element according to claim 11.

Description

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0076] Specific embodiments are further illustrated by the following examples to demonstrate the technical approaches of the present invention. Those skilled in the art should understand that the illustrative examples are helpful to understand the present invention; however, they should not be construed as being limiting to the scope of the present invention.

[0077] The compounds whose synthesis methods are not mentioned in the present invention are commercially available products used as raw materials. The solvents and agents used in the present invention, for example, chemical agents such as tetrahydrofuran, potassium hydroxide, nitrobenzene, palladium catalyst and the like, can be purchased in the chemical product market in China, for example, purchased from Sinopharm Chemical Reagent Co., Ltd.; Tokyo Chemical Industry (TCI) Co., Ltd.; Bide Pharmatech Ltd.; J&K Scientific Ltd. and the like. In addition, these compounds can also be synthesized with a well-known method by those skilled in the art.

Preparation Example of Compound of Formula (1)

[0078] ##STR00100## ##STR00101##

[0079] Synthesis of M6-B: In a three-necked bottle of 25 milliliters (mL), M6-A (10 millimoles (mmol)), nitrobenzene (10 mmol), potassium hydroxide (22 mmol), copper(I) thiocyanate (1 mmol) and anhydrous tetrahydrofuran (10 mL) were added, nitrogen gas was purged for three times, and heated to 90° C. under nitrogen gas protection to react for 48 hours (h). After the reaction ended, the reaction mixture was quenched by water, the reaction system was extracted by ethyl acetate, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-B (1.34 g, 49% yield).

[0080] Synthesis of M6-B′: In a three-necked bottle of 50 mL, 2-bromo chlorobenzaldehyde (10 mmol), bis(pinacolato)diboron (12 mmol), potassium acetate (100 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.2 mmol) and 1,4-dioxane (25 mL) were added, nitrogen gas was purged, and heated to 100° C. under nitrogen gas protection for reaction. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride to give a crude product. The crude product was purified by column chromatography (methylene dichloride:n-hexane=1:50 (volume ratio)), to obtain M6-B′ (1.7 g, 64% yield).

[0081] Synthesis of M6-C: In a three-necked bottle of 50 mL, M6-B (10 mmol), M6-B′ (10 mmol), sodium bicarbonate (20 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), tetrahydrofuran (20 mL) and water (10 mL) were added, nitrogen gas was purged, and heated to 60° C. under nitrogen gas protection to react overnight. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-C (3.06 g, 92% yield).

[0082] Synthesis of M6-D: In a three-necked bottle of 50 mL, M6-C (10 mmol), (methoxymethyl)triphenylphosphonium chloride (20 mmol) and tetrahydrofuran (10 mL) were added, and the temperature was reduced to 0° C. Potassium tert-butoxide (2 mmol) was resolved in 5 mL tetrahydrofuran. The three-necked bottle was purged with nitrogen gas. Under nitrogen gas protection, the potassium tert-butoxide solution was added dropwise at 0° C. to obtain a mixture. After the addition, the mixture was stirred to react for half an hour. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-D (1.8 g, 50% yield).

[0083] Synthesis of M6-E: In a three-necked bottle of 25 mL, M6-D (1 mmol) and hexafluoroisopropanol (5 mL) were added, the temperature was reduced to 0° C., and nitrogen gas was purged. Under nitrogen gas protection, trifluoromethanesulfonic acid (1 mL) was added dropwise to obtain a mixture, and the mixture was stirred to react for half an hour to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-E (0.24 g, 73% yield).

[0084] Synthesis of M6-F: In a three-necked round-bottom flask of 50 mL, M6-E (10 mmol), bis(pinacolato)diboron (12 mmol), sodium acetate (20 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.5 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.5 mmol) were added, then 1,4-dioxane (20 mL) was added, nitrogen gas was purged for three times, and heated to 100° C. under nitrogen gas protection for reaction. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-F (3.24 g, 77% yield).

[0085] Synthesis of M6: In a three-necked round-bottom flask of 100 mL, a stir bar was put at the bottom and a refluxing tube was connected on the top. The flask was dried and purged with nitrogen gas, and M6-F (10 mmol), M6-G (10 mmol, CAS1689576-03-1), sodium bicarbonate (23 mmol), tetrakis(triphenylphosphine)palladium (0.5 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.5 mmol), toluene (25 mL), ethanol (7 mL) and water (7 mL) were separately added, nitrogen gas was purged for three times, and heated to 80° C. under nitrogen gas protection to react for 8 h. After the reaction ended, the reaction mixture was extracted by ethyl acetate, and the resulting extract was dried by magnesium sulfate, filtered, and dried by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:10 (volume ratio)), to obtain compound M6 (4.13 g, 67% yield).

[0086] Anal. Calcd. C.sub.41H.sub.26N.sub.6: C, 81.71; H, 4.35; N, 13.94. Found: C, 81.78; H, 4.33; N, 13.89. HRMS (ESI) m/z [M+H].sup.+: Calcd.: 602.22. Found: 603.40.

##STR00102## ##STR00103##

[0087] Synthesis of M160-B″: Similar to the synthesis of M6-B′, with the difference that 2-bromo-5-chlorobenzaldehyde is used to replace 2-bromo chlorobenzaldehyde, to obtain M160-B″ (1.60 g, 60% yield).

[0088] Synthesis of M160-C: Similar to the synthesis of M6-C, with the difference that 4-fluoro-2-formylbenzeneboronic acid pinacol ester is used to replace 5-fluoro-2-formylbenzeneboronic acid pinacol ester, to obtain M160-C (2.13 g, 64% yield).

[0089] Synthesis of M160-D: Similar to the synthesis of M6-D, with the difference that M160-C is used to replace M6-C, to obtain M160-D (3.21 g, 89% yield).

[0090] Synthesis of M160-E: Similar to the synthesis of M6-E, with the difference that M160-D is used to replace M6-D, to obtain M160-E (0.16 g, 48% yield).

[0091] Synthesis of M160-F: Similar to the synthesis of M6-F, with the difference that M160-E is used to replace M6-E, to obtain M160-F (4.00 g, 95% yield).

[0092] Synthesis of compound M160: Similar to the synthesis of compound M6, with the difference that M160-F is used to replace M6-F, and M160-G is used to replace M6-G, to obtain compound M160 (4.70 g, 78% yield).

[0093] Anal. Calcd. C.sub.41H.sub.26N.sub.6: C, 81.71; H, 4.35; N, 13.94. Found: C, 81.73; H, 4.37; N, 13.90. HRMS (ESI) m/z (M.sup.+): Calcd.: 602.22. Found: 603.29.

[0094] The corresponding products shown in Table 1 were prepared by the above-mentioned preparation method using the Material 1 and Material 2 as raw materials. The structure and characteristic data of the products are shown in Table 2.

TABLE-US-00001 TABLE 1 Material 1 Material 2 Product Yield (%) [00104] [00105] [00106] 65 [00107] [00108] [00109] 67 [00110] [00111] [00112] 74 [00113] [00114] [00115] 65 [00116] [00117] [00118] 68 [00119] [00120] [00121] 68 [00122] [00123] [00124] 61

TABLE-US-00002 TABLE 2 HRMS (ESI) Elemental analysis m/z [M + H].sup.+ Compound Calcd. Found Calcd. Found M46 C, 79.85; H, 3.92; C, 79.92; H, 3.91; 616.20 617.26 N, 13.63; N, 13.59; M41 C, 79.21; H, 4.70; C, 79.24; H, 4.71; 621.23 622.26 N, 13.52; N, 13.48; M23 C, 82.22; H, 4.70; C, 82.16; H, 4.72; 642.25 643.25 N, 13.08; N, 13.12; M97 C, 81.49; H, 4.07; C, 81.53; H, 4.08; 692.23 693.20 N, 12.13; N, 12.08; M117 C, 83.46; H, 4.38; C, 83.39; H, 4.40; 575.21 576.24 N, 12.17; N, 12.21; M93 C, 81.93; H, 4.09; C, 81.89; H, 4.11; 615.21 616.17 N, 11.37; N, 11.40; M31 C, 79.98; H, 4.09; C, 80.04; H, 4.08; 615.22 616.16 N, 15.92; N, 15.88;

Preparation Example of Compound of Formula (2)

[0095] ##STR00125##

[0096] Synthesis of compound N4: In a three-necked bottle of 25 mL, nitrogen gas was purged, N4-A (1 mmol, CAS 2085325-19-3), N4-B (1 mmol, CAS 102113-98-4), sodium tert-butoxide (2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.02 mmol), 50% tri-tert-butylphosphine solution (0.1 mmol) and toluene 8 mL was added, and stirred under reflux to react. After the reaction ended, the reaction mixture was cooled to room temperature, and the organic layer was extracted by ethyl acetate and H.sub.2O. The extracted organic layer was dried by MgSO.sub.4, filtered, and the filtrate was concentrated under vacuum to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain compound N4 (0.43 g, 69% yield).

[0097] Anal. Calcd. C.sub.45H.sub.30N.sub.2O: C, 87.92; H, 4.92; N, 4.56. Found: C, 87.97; H, 4.90; N, 4.53. FIRMS (ESI) m/z [M+H].sup.+: Calcd.: 614.24. Found: 615.33.

##STR00126##

[0098] Synthesis of N33: In a two-necked round-bottom flask of 25 mL, a stir bar was put at the bottom and a refluxing tube was connected on the top. The flask was dried and purged with nitrogen gas, and N33-A (1 mmol), N33-B (1 mmol, CAS 2468159-90-0), potassium carbonate (1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), toluene (7 mL), and water (2 mL) were separately added, nitrogen gas was purged for three times, and heated to 85° C. under nitrogen gas protection to react for 10 h. After the reaction ended, the reaction mixture was extracted by ethyl acetate, and the resulting extract was dried by magnesium sulfate, filtered, and dried by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:10 (volume ratio)), to obtain compound N33 (0.44 g, 63% yield).

[0099] Anal. Calcd. C.sub.45H.sub.28N.sub.2O.sub.2: C, 85.97; H, 4.49; N, 4.46. Found: C, 85.88; H, 4.52; N, 4.48. HRMS (ESI) m/z (M.sup.+): Calcd.: 628.22 Found: 629.10.

[0100] Compounds in Table 3 were synthesized by the same synthesis method for preparing compound N33. The raw materials and resulting products are shown in Table 3. The structure and characteristic data of the products are shown in Table 4.

TABLE-US-00003 TABLE 3 Material 1 Material 2 Product Yield % [00127] [00128] [00129] 71 [00130] [00131] [00132] 69 [00133] [00134] [00135] 67 [00136] [00137] [00138] 68

TABLE-US-00004 TABLE 4 HRMS (ESI) Elemental analysis m/z [M + H].sup.+ Compound Calcd. Found Calcd. Found N14 C, 87.87; H, 5.13; C, 87.90; H, 5.10; 628.25 629.32 N, 4.46; N, 4.47; N22 C, 85.97; H, 4.49; C, 85.91; H, 4.52; 628.22 629.32 N, 4.46; N, 4.45; N44 C, 87.92; H, 4.92; C, 87.96; H, 4.89; 614.24 615.15 N, 4.56 N, 4.55 N56 C, 86.10; H, 4.66; C, 86.07; H, 4.65; 627.23 628.34 N, 6.69 N, 6.72

Application Examples

[0101] An organic electroluminescence element (such as OLED) with the following layer structure was provided: base (indium tin oxide (ITO, as an anode) coated glass substrate)/hole injection layer (HIL)/hole transport layer (HTL)/emitting layer (EML)/electron transport layer (ETL)/electron injection layer (EIL), and the cathode at last.

[0102] The materials needed to prepare OLED are listed below, wherein the REF-1 is comparative compound 1:

##STR00139## ##STR00140##

[0103] The above-mentioned organic electroluminescence elements were prepared by the following steps:

[0104] (1) Cleaning the substrate: a glass substrate coated with transparent ITO layer (the anode) was ultrasonicated in an aqueous detergent (the content and concentration of the aqueous detergent: an ethylene glycol solvent of ≤10 percent by weight (wt %), triethanolamine of ≤1 wt %), washed in deionized water, degreased in an acetone/ethanol mixed solvent (volume ratio=1:1) by ultrasonication, baked in a clear environment until water was completely removed, and washed by ozone under ultraviolet light;

[0105] (2) Depositing organic emitting functional layers:

[0106] The glass substrate with the anode was placed in a chamber, and the chamber was vacuumized until 1×10.sup.−6 Pascal (Pa) to 2×10.sup.−4 Pa, and a mixture of HAT(CN).sub.6 and HT (mass ratio of HAT(CN).sub.6 and HT is 3:97) was deposited on the anode layer in vacuum to form a hole injection layer, in which the deposited thickness was 10 nanometers (nm).

[0107] A hole transport layer was deposited on the hole injection layer, in which the deposited thickness was 80 nm.

[0108] An emitting layer was deposited on the hole transport layer. Specifically, the preparation method was: the light-emitting host material and a guest material were co-deposited in vacuum, in which the total deposited thickness was 30 nm.

[0109] An electron transport layer was deposited on the emitting layer. Specifically, the preparation method was: BPhen and LiQ were co-deposited in vacuum, in which the total deposited thickness was 30 nm.

[0110] An electron injection layer was deposited on the electron transport layer, in which the total deposited thickness was 1 nm.

[0111] Al (as cathode) was deposited on the electron injection layer 6, in which the deposited thickness was 80 nm.

[0112] The materials (mat.) of each layer in the element and parameters such as thickness (thk.) of Element Examples 1 to 11 (E1 to E11) and Comparative Element Examples 1 to 2 (CE1 to CE2) are shown in Table 5.

TABLE-US-00005 TABLE 5 Cath- HTL ETL EIL ode HIL mat./ mat./ EML mat./ mat./ mat./ mat./ No. thk. thk. thk. thk. thk. thk. E1 HAT(CN).sub.6: HT/ compound M6: BPhen: LiQ/ Al/ HT (mass 80 nm compound N44: LiQ 1 nm 80 nm ratio3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E2 HAT(CN).sub.6: HT/ compound M6: BPhen: LiQ/ Al/ HT (mass 80 nm compound N4: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E3 HAT(CN).sub.6: HT/ compound M160: BPhen: LiQ/ Al/ HT (mass 80 nm compound N14: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E4 HAT(CN).sub.6: HT/ compound M46: BPhen: LiQ/ Al/ HT (mass 80 nm compound N4: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E5 HAT(CN).sub.6: HT/ compound M41: BPhen: LiQ/ Al/ HT (mass 80 nm compound N33: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E6 HAT(CN).sub.6: HT/ compound M23: BPhen: LiQ/ Al/ HT (mass 80 nm compound N56: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E7 HAT(CN).sub.6: HT/ compound M97: BPhen: LiQ/ Al/ HT (mass 80 nm compound N44: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E8 HAT(CN).sub.6: HT/ compound M117: BPhen: LiQ/ Al/ HT (mass 80 nm compound N4: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E9 HAT(CN).sub.6: HT/ compound M93: BPhen: LiQ/ Al/ HT (mass 80 nm compound N22: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E10 HAT(CN).sub.6: HT/ compound M31: BPhen: LiQ/ Al/ HT (mass 80 nm compound N4: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 47.5:47.5:5)/ 30 nm 30 nm E11 HAT(CN).sub.6: HT/ compound M46: BPhen: LiQ/ Al/ HT (mass 80 nm compound N4: LiQ 1 nm 80 nm ratio 3:97)/ (piq).sub.2Ir(acac) (mass 10 nm (mass ratio ratio 1:1)/ 13:6:1)/ 30 nm 30 nm CE1 HAT(CN).sub.6: HT/ CBP: compound BPhen: LiQ/ Al/ HT (mass 80 nm N4: (piq).sub.2Ir(acac) LiQ 1 nm 80 nm ratio 3:97)/ (mass ratio (mass 10 nm 47.5:47.5:5)/ ratio 1:1)/ 30 nm 30 nm CE2 HAT(CN).sub.6: HT/ REF-1: compound BPhen: LiQ/ Al/ HT (mass 80 nm N4: (piq).sub.2Ir(acac) LiQ 1 nm 80 nm ratio 3:97)/ (mass ratio (mass 10 nm 47.5:47.5:5)/ ratio 1:1) 30 nm 30 nm

[0113] Characteristic Tests of Elements:

[0114] Instruments: the characteristics such as current, voltage, luminance, emission spectrum and the like of the elements of the above Element Examples 1 to 11 and Comparative Element Examples 1 to 2 were synchronously tested by PR 650 SpectraScan Colorimeter and Keithley K 2400 SourceMeter;

[0115] Conditions for testing electrooptical characteristics: a current density of 10 milliamperes/square centimeter (mA/cm.sup.2) under room temperature;

[0116] Service life test: tested with a current density of 20 mA/cm.sup.2 under room temperature, and the time period recorded when the luminance of the tested element was reduced to 98% of the original luminance (in hour).

[0117] The test results of the elements are shown in Table 6.

TABLE-US-00006 TABLE 6 Driving Current Service No. voltage (V) efficiency (Cd/A) life (h) E1 3.89 23 235 E2 3.87 25 250 E3 3.88 24 240 E4 3.93 23 230 E5 3.87 20 218 E6 3.96 22 245 E7 3.95 21 220 E8 3.92 24 225 E9 3.90 24 240 E10 3.88 23 245 E11 3.90 24 235 CE1 4.34 15 97 CE2 4.13 17 125

[0118] From Table 6, it is clear that the organic material composition of the present invention obviously increases the current efficiency. When the organic material composition is used as the material of an organic functional layer, the element has a lower driving voltage (3.96 voltages (V) or lower), a higher current efficiency (20 Candelas/Ampere (Cd/A) or more) and a longer service life (218 h or more).

[0119] The applicant claims herein that even though the organic material composition of the present invention and the applications thereof are demonstrated by the above examples, the scope of the present invention is not limited by these examples. That is to say, it does not mean that the present invention has to be carried out based on the above examples. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of materials, addition of auxiliary components, selection of specific means and the like are all within the scope of protection and disclosure of the present invention.