Organic electronic material

Abstract

The present invention also relates to an organic electronic material with the structure of formula (I). It is a kind of hole transport and injection material with good thermal stability, high hole mobility and excellent solubility. The OLEDs prepared thereof have the advantages such as good light emitting efficiency, excellent color purity and long lifetime. ##STR00001##

Claims

1. An organic electronic material has the following structural formula (I): ##STR00048## wherein, R.sub.1-R.sub.3 independently represent hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C6-C30 aryl unsubstituted or substituted by one or more substituent group R, C3-C30 heteroaryl containing one or more heteroatoms unsubstituted or substituted by one or more substituent group R, C2-C8 alkenyl unsubstituted or substituted by one or more substituent group R, C2-C8 alkynyl unsubstituted or substituted by one or more substituent group R, C8-C30 diaryl vinyl unsubstituted or substituted by one or more substituent group R, C8-C30 diaryl ethynyl, trialkyl silicon unsubstituted or substituted by one or more substituent group R, C6-C30 triaryl silicon unsubstituted or substituted by one or more substituent group R, C6-C30 diaryl phosphonoso unsubstituted or substituted by one or more substituent group R, C6-C30 aryl carbonyl unsubstituted or substituted by one or more substituent group R, C6-C30 aryl sulfenyl unsubstituted or substituted by one or more substituent group R, C6-C30 aryl fused ring unsubstituted or substituted by one or more substituent group R, C6-C30 substituted or unsubstituted heteroatom-containing aryl fused ring, C6-C30 carbazolyl unsubstituted or substituted by one or more substituent group R, C6-C30 diaryl amine unsubstituted or substituted by one or more substituent group R, or a spiral structure formed between two R.sub.2 groups, and the said heteroatoms are B, O, S, N, and Se; wherein Ar.sub.1-Ar.sub.2 represent independently C6-C30 aryl containing one or more substituent group R, aryl fused ring unsubstituted or substituted by one or more substituent group R, C6-C30 carbazolyl unsubstituted or substituted by one or more substituent group R, or C6-C30 tri-aromatic amine unsubstituted or substituted by one or more substituent group R; and wherein, R represents independently alkyl, five-or six-membered ring aryl, alkoxy, deuterium, halogen, cyano, nitro, or amino.

2. The organic electronic material according to claim 1, wherein: R.sub.1-R.sub.3 are independently selected from hydrogen, halo, C1-C8 alkyl, C6-C30 phenyl group unsubstituted or substituted by one or more substituent group R, diaryl amine unsubstituted or substituted by one or more substituent group R, C6-C30 aryl fused ring unsubstituted or substituted by one or more substituent group R, C6-C30 carbazolyl unsubstituted or substituted by one or more substituent group R, or two R.sub.2 forming a spirofluorene structure; Ar.sub.1-Ar.sub.2 represent independently C6-C30 aryl containing one or more substituent group R, aryl fused ring unsubstituted or substituted by one or more substituent group R, C6-C30 carbazolyl unsubstituted or substituted by one or more substituent group R, C6-C30 tri-aromatic amine unsubstituted or substituted by one or more substituent group R; and R independently represents an alkyl group, a five- or six-membered ring of aryl, alkoxy, or halogen.

3. The organic electronic material according to claim 2, wherein: R.sub.1-R.sub.3 are independently selected from hydrogen, C1-C8 alkyl group, one or more C1-C3 alkyl, C1-C3 alkoxy, aryl-substituted or unsubstituted phenyl, one or more C1-C3 alkyl, C1-C3 alkoxy, aryl-substituted or unsubstituted naphthyl, one or more C1-C3 alkyl, C1-C3 alkoxy, aryl-substituted or unsubstituted carbazolyl or a spiral structure is formed between two R.sub.2 groups.

4. The organic electronic material according to claim 3, wherein: R.sub.1, R.sub.2 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, cyclohexyl, n-octyl, isooctyl, C1-C3 alkyl substituted or unsubstituted phenyl, C1-C3 alkoxy substituted or unsubstituted phenyl, naphthyl or a spiral structure is formed between two R.sub.2 groups, one or more methyl, phenyl substituted or unsubstituted diaryl amine, one or more methyl, phenyl substituted or unsubstituted carbazolyl; and R.sub.3 is independently selected from hydrogen, C1-C8 alkyl, C1-C3 substituted or unsubstituted phenyl.

5. The organic electronic material according to claim 4, wherein: R.sub.1, R.sub.2 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, cyclohexyl, n-octyl, iso-octyl, phenyl, tolyl; and R.sub.3 is independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkyl substituted or unsubstituted phenyl.

6. The organic electronic material according to claim 5, wherein: R.sub.3 is hydrogen, methyl, phynyl; R.sub.1, R.sub.2 are independently selected from hydrogen, methyl, t-butyl, phenyl; R1, R2 are independently selected to form a spiro structure between hydrogen, methyl, t-butyl, phenyl or a spiral structure is formed between two R.sub.2 groups; and Ar.sub.1-Ar.sub.2 are independently expressed as any one of the groups in the table below TABLE-US-00003

7. The organic electronic material according to claim 5, wherein the compound described in formula I has any of the following structures: ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090##

8. The organic electronic material according to claim 7, wherein: R.sub.1, R.sub.2, R.sub.3 are independently selected from hydrogen, methyl, phenyl; and Ar1-Ar2 independently represent phenyl, naphthyl or biphenyl.

9. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 1; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

10. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 2; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

11. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 3; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

12. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 4; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

13. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 5; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

14. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 6; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

15. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 7; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

16. An article that includes an organic electronic material, the article comprising: the organic electronic material of claim 8; and a structure that enables the article to be used in at least one of: an organic light-emitting diode (OLED) application; organic solar cells; organic thin film transistors; and organic photoreceptors.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 is a structural chart of the device, of which, 10 denotes a glass substrate, 20 denotes an anode, 30 denotes hole injection layer, 40 denotes hole transport layer, 50 denotes light emitting layer, 60 denotes electron transport layer, 70 denotes electron injection layer, 80 denotes cathode.

(2) FIG. 2 is the chart of device current density and voltage in Embodiment 3, Embodiment 5 and Comparative Example 1

(3) FIG. 3 is the chart of device light-emitting efficiency and current density in Embodiment 3, Embodiment 5 and Comparative Example 1

(4) FIG. 4 is the electrospray ionization mass spectrum of compound 2 in Embodiment 1.

DETAILED DESCRIPTIONS OF THE PREFERRED EMBODIMENTS

(5) In the following, the present invention is described in details by combining the following examples.

(6) Embodiment 1

(7) Synthesis of Compound 2

(8) ##STR00045## ##STR00046##
Synthesis of Intermediate 1-1

(9) In a 1 L three-necked flask, add the compound methyl anthranilate and bromoiodobenzene, cuprous iodide, potassium carbonate, o-dichlorobenzene; with the protection of nitrogen, heat them to 180 C. for 24 h, cooled to 100 C., then filter. Remove the solvent in the filtrate by pressure reduction, and then separate it to get compound 1-1 through column chromatography, with a yield 92%, HPLC purity 96%.

(10) Synthesis of Intermediate 1-2

(11) In a 1 L three-necked flask, add the compound 1-1 and tetrahydrofuran. With the protection of nitrogen, cool to 0 C., then dropwise add the methulmagnesium bromide, slowly heat to the room temperature, react overnight, and then add 1N hydrochloric acid solution, extract with ethyl acetate, dry, concentrate it, and then separate to get compound 1-2 through column chromatography, with a yield 83%, HPLC purity 93%.

(12) Synthesis of Intermediate 1-3

(13) In a 1 L three-necked flask, add the compound 1-2, phosphoric acid, stir to react completely, then add them to the water to filter. The filter cake is washed twice with methanol solution, to get the intermediate 1-3, with a yield 80% and HPLC content 90%.

(14) Synthesis of Intermediate 1-4

(15) In a 1 L three-necked flask, add compound 1-3 and iodobenzene, potassium tert-butoxide, tri-tert-butylphosphine, xylene; with the protection of nitrogen, heat them to 120 C. for 24 hours, cool down to room temperature, filter. Remove the solvent in the filtrate by pressure reduction, and then separate it to get compound 1-4 through column chromatography.

(16) Synthesis of Compound 2

(17) In a 1 L three-necked flask, add compound 1-4 and biphenyl diamine, potassium tert-butoxide, tri-tert-butylphosphine and xylene. With the protection of nitrogen, heat to 120 C. for 24 hours, cool down to 100 C., filter. Remove the solvent in the filtrate by pressure reduction, and then separate it to get compound 2 through column chromatography.

(18) ESI-MS m/z 902.4.

(19) Embodiment 2

(20) Preparation of OLED

(21) Prepare OLED Using the OEL Material in the Invention

(22) Firstly, the ITO transparent conductive glass substrate 10 (with the anode 20 above) is subject to washing by detergent solution ethanol, acetone and deionized water, and then treated by oxygen plasma for 30 seconds.

(23) Then, the compound 2 with 10 nm thick is evaporated on ITO as the hole injection layer 30.

(24) Then, the compound NPB is evaporated to form hole transport layer 40 with thickness of 60 nm.

(25) Then, the compound Alq.sub.3 with thickness of 50 nm is evaporated on the hole transport layer as the light emitting layer 50.

(26) Then, the Alq.sub.3 with thickness of 10 nm is evaporated on light emitting layer as the electron transport layer 60.

(27) Finally, 1 nm Liq is evaporated as the electron injection layer 70 and 100 nm Al as the device cathode 80.

(28) Embodiment 3

(29) Preparation of OLED

(30) Prepare OLED Using the OEL Material in the Invention

(31) Firstly, the ITO transparent conductive glass substrate 10 (with the anode 20 above) is subject to washing by detergent solution ethanol, acetone and deionized water, and then treated by oxygen plasma for 30 seconds.

(32) Then, the compound 2 with 10 nm thick is evaporated on ITO as the hole injection layer 30.

(33) Then, the compound NPB is evaporated to form hole transport layer 40 with thickness of 60 nm.

(34) Then, the compound Alq.sub.3 with thickness of 50 nm is evaporated on the hole transport layer as the light emitting layer 50.

(35) Then, the Alq.sub.3 with thickness of 10 nm is evaporated on light emitting layer as the electron transport layer 60.

(36) Finally, 1 nm Liq is evaporated as the electron injection layer 70 and 100 nm Al as the device cathode 80.

(37) Embodiment 4

(38) Preparation of OLED

(39) Prepare OLED Using the OEL Material in the Invention

(40) Firstly, the ITO transparent conductive glass substrate 10 (with the anode 20 above) is subject to washing by detergent solution ethanol, acetone and deionized water, and then treated by oxygen plasma for 30 seconds.

(41) Then, the compound 2 with 10 nm thick is evaporated on ITO as the hole injection layer 30.

(42) Then, the compound NPB is evaporated to form hole transport layer 40 with thickness of 60 nm.

(43) Then, the compound Alq.sub.3 with thickness of 50 nm is evaporated on the hole transport layer as the light emitting layer 50.

(44) Then, the Alq.sub.3 with thickness of 10 nm is evaporated on light emitting layer as the electron transport layer 60.

(45) Finally, 1 nm Liq is evaporated as the electron injection layer 70 and 100 nm Al as the device cathode 80.

(46) Embodiment 5

(47) Preparation of OLED

(48) Prepare OLED Using the OEL Material in the Invention

(49) Firstly, the ITO transparent conductive glass substrate 10 (with the anode 20 above) is subject to washing by detergent solution ethanol, acetone and deionized water, and then treated by oxygen plasma for 30 seconds.

(50) Then, the compound 2 with 10 nm thick is evaporated on ITO as the hole injection layer 30.

(51) Then, the compound NPB is evaporated to form hole transport layer 40 with thickness of 60 nm.

(52) Then, the compound Alq.sub.3 with thickness of 50 nm is evaporated on the hole transport layer as the light emitting layer 50.

(53) Then, the Alq.sub.3 with thickness of 10 nm is evaporated on light emitting layer as the electron transport layer 60.

(54) Finally, 1 nm Liq is evaporated as the electron injection layer 70 and 100 nm Al as the device cathode 80.

(55) Comparative Example 1

(56) Preparation of OLED

(57) Prepare OLED Using the OEL Material in the Invention

(58) Firstly, the ITO transparent conductive glass substrate 10 (with the anode 20 above) is subject to washing by detergent solution ethanol, acetone and deionized water, and then treated by oxygen plasma for 30 seconds.

(59) Then, the compound NPB is evaporated on ITO to form hole transport layer 40 with thickness of 60 nm.

(60) Then, the compound Alq.sub.3 with thickness of 50 nm is evaporated on the hole transport layer as the light emitting layer 50.

(61) Then, the Alq.sub.3 with thickness of 10 nm is evaporated on light emitting layer as the electron transport layer 60.

(62) Finally, 1 nm Liq is evaporated as the electron injection layer 70 and 100 nm Al as the device cathode 80.

(63) The structural form of device

(64) ##STR00047##

(65) The light-emitting data of device are shown in FIGS. 2 and 3.

(66) Table 1 shows the CIE coordinates of device in Embodiments 2-5 in the present invention

(67) TABLE-US-00002 CIE.sub.x, CIE.sub.y Compound 2, 0 nm Comparative example 1 0.35, 0.53 Compound 2, 10 nm Embodiment 2 0.35, 0.53 Compound 2, 20 nm Embodiment 3 0.33, 0.53 Compound 2, 30 nm Embodiment 4 0.33, 0.53 Compound 2, 40 nm Embodiment 5 0.32, 0.54

(68) In Comparative Example 1, in the absence of organic light-emitting material with formula (I) as the hole injection material, the light-emitting efficiency is only 2.7 cd/A; however, after the hole injection material is added, its effect is significantly improved. In Embodiment 5, the organic light-emitting material with formula (I) is used as the hole injection material with 40 nm in thickness, and the light-emitting efficiency is increased by over 37% compared to Embodiment 1, which is up to 3.7 cd/A.

(69) Experimental results show that, the organic light-emitting material with structural formula (I) has a good thermal stability, high hole mobility, high light-emitting efficiency, high light-emitting purity. The OLEDs made from this organic light-emitting material will have advantages of good light-emitting efficiency, excellent color purity and long lifetime.