OXYGEN HETEROCYCLIC COMPOUND, APPLICATION THEREOF AND ELECTRONIC DEVICE USING THE SAME

Abstract

The present disclosure provides an oxygen heterocyclic compound, an application thereof, and an electronic device using the same. The oxygen heterocyclic compound has a structural formula as represented by following formula 1:

##STR00001##

The oxygen heterocyclic compound comprises an aromatic amine portion and an oxygen heterocyclic portion. The aromatic amine portion effectively promotes the hole injection and transport performance. The oxygen heterocyclic portion is conducive to the formation of molten evaporation materials.

Claims

1. An oxygen heterocyclic compound, having a structural formula as represented by following formula 1: ##STR00082## wherein, Ar.sub.1 and Ar.sub.2 are independently selected from the group consisting of single or multiple substituted or unsubstituted aryl groups, and single or multiple substituted or unsubstituted heteroaryl groups; or Ar.sub.1 and Ar.sub.2 together form single or fused aromatic or heterocyclic ring when Ar.sub.1 and Ar.sub.2 are adjacent aryl groups or heteroaryl groups connected to each other, wherein heteroatoms of the heteroaryl groups are O, N, F, S, or Si; and Ar.sub.3 and Ar.sub.4 are independently selected from the group consisting of C1 to C22 alkyl groups, C1 to C22 alkoxy groups, C1 to C22 heteroalkyl groups, single or multiple substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or Ar.sub.3 and Ar.sub.4 together form a single or fused aromatic or heterocyclic ring when Ar.sub.3 and Ar.sub.4 are adjacent aryl groups or heteroaryl groups connected to each other, wherein heteroatoms of the heteroaryl groups are O, N, F, S, or Si.

2. The oxygen heterocyclic compound according to claim 1, wherein the oxygen heterocyclic compound has a structural formula represented by following formula 2: ##STR00083##

3. The oxygen heterocyclic compound according to claim 1, wherein Ar.sub.1 and Ar.sub.2 are independently represented by any of following formula 301 to formula 332: ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091##

4. The oxygen heterocyclic compound according to claim 1, wherein Ar.sub.3 and Ar.sub.4 are independently represented by any of following formula 301 to formula 332 and formula 401 to formula 403: ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099##

5. The oxygen heterocyclic compound according to claim 2, wherein the oxygen heterocyclic compound has a structural formula represented by any of following formula 501 to formula 508: ##STR00100## ##STR00101## ##STR00102##

6. The oxygen heterocyclic compound according to claim 2, wherein the oxygen heterocyclic compound has a structure as represented by any of following formula 601 to formula 617: ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108##

7. The oxygen heterocyclic compound according to claim 2, wherein the oxygen heterocyclic compound has a structure as represented by any of following formula 701 to formula 722: ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115##

8. The oxygen heterocyclic compound according to claim 2, wherein the oxygen heterocyclic compound has a structure as represented by any of following formula 801 to formula 819: ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120##

9. A use of an oxygen heterocyclic compound according to any of claims 1 as being an electroluminescent organic material in an electronic device.

10. An electronic device, comprising a base, an anode, a cathode, and one or more of organic material layers disposed between the anode and the cathode, wherein at least one of the organic layers comprises the oxygen heterocyclic compound according to any of claims 1.

Description

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[0018] An oxygen heterocyclic compound and an electronic device using the same provided by embodiments of the present disclosure will be explained and described in detail below.

[0019] An oxygen heterocyclic compound according to one embodiment of the present disclosure has a structural formula as represented by following formula 1:

##STR00039##

[0020] In formula 1, Ar.sub.1 and Ar.sub.2 are independently selected from the group consisting of single or multiple substituted or unsubstituted aryl groups, and single or multiple substituted or unsubstituted heteroaryl groups; or Ar.sub.1 and Ar.sub.2 together form single or fused aromatic or heterocyclic ring when Ar.sub.1 and Ar.sub.2 are adjacent aryl groups or heteroaryl groups connected to each other, wherein heteroatoms of the heteroaryl groups are O, N, F, S, or Si; and Ar.sub.3 and Ar.sub.4 are independently selected from the group consisting of C1 to C22 alkyl groups, C.sub.1 to C22 alkoxy groups, C1 to C22 heteroalkyl groups, single or multiple substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups, or Ar.sub.3 and Ar.sub.4 together form a single or fused aromatic or heterocyclic ring when Ar.sub.3 and Ar.sub.4 are adjacent aryl groups or heteroaryl groups connected to each other, wherein heteroatoms of the heteroaryl groups are O, N, F, S, or Si.

[0021] As being a preferred embodiment of the present disclosure, the oxygen heterocyclic compound may have a structural formula represented by following formula 2:

##STR00040##

[0022] It can be understood that the aromatic amine portion of the oxygen heterocyclic compound in the preferred embodiment has a fixed substitution position.

[0023] As being a preferred embodiment of the present disclosure, Ar.sub.1 and Ar.sub.2 may be independently represented by any of following formula 301 to formula 332:

##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048##

[0024] As being a preferred embodiment of the present disclosure, Ar.sub.1 and Ar.sub.4 are independently represented by any of above formula 301 to formula 332 and following formula 401 to formula 403:

##STR00049##

[0025] As being a further preferred embodiment of the present disclosure, the oxygen heterocyclic compound may have a structural formula represented by any of following formula 501 to formula 508:

##STR00050## ##STR00051## ##STR00052##

[0026] As being another further preferred embodiment of the present disclosure, the oxygen heterocyclic compound may have a structure as represented by any of following formula 601 to formula 617:

##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058##

[0027] As being another further preferred embodiment of the present disclosure, the oxygen heterocyclic compound may have a structure as represented by any of following formula 701 to formula 722:

##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065##

[0028] As being another further preferred embodiment of the present disclosure, the oxygen heterocyclic compound may have a structure as represented by any of following formula 801 to formula 819:

##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070##

[0029] Another embodiment of the present disclosure provides an application of the abovementioned oxygen heterocyclic compound as being an electroluminescent organic material in an electronic device.

[0030] A further embodiment of the present disclosure provides an electronic device, comprising a base, an anode, a cathode, and one or more of organic material layers disposed between the anode and the cathode, wherein at least one of the organic layers comprises the oxygen heterocyclic compound oxygen heterocyclic compound according to the above embodiment. It is characterized that the organic layers may include a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a light-emitting layer. Herein, the electronic device may be an electroluminescent device, for example, an organic light-emitting diode device.

[0031] In the following, the preparation methods of the oxygen heterocyclic compounds provided in the above embodiments of the present disclosure are described.

Embodiment 1

[0032] The synthesis of Target structure 1 of the oxygen heterocyclic compound is shown in process formula 9:

##STR00071##

[0033] The preparation method of Target structure 1 of the oxygen heterocyclic compound provided by Embodiment 1 is as follows:

[0034] Compound (1) (3 mmol), Pd(OAc).sub.2 (0.15 mmol), PPh.sub.3(0.3 mmol), CsCO.sub.3(6.0 mmol), and 50 mL of toluene were added to a 100 mL two-necked flask, then stirred and heated to 100° C. under argon atmosphere to react for 12 h. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 2.7 mmol of an intermediate compound (2) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 90%.

[0035] The product of the previous step-compound (2), magnesium (Mg, 3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, Benzophenone (3 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.9 mmol of an intermediate compound (3) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 70%.

[0036] The obtained intermediate compound (3) was added into 100 mL of acetonitrile, and 2 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.3 mmol of Target structure 1 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 77%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 501.63; Measured value m/z, 501.42. Elemental analysis (EA): Calculated value C, 88.59; H, 5.43; N, 2.79; Measured value C, 88.25; H, 5.51; N, 2.83.

Embodiment 2

[0037] The synthesis of Target structure 2 of the oxygen heterocyclic compound is shown in process formula 10:

##STR00072##

[0038] In Embodiment 2, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 2 of the oxygen heterocyclic compound provided by Embodiment 2 is as follows:

[0039] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (4) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 2.0 mmol of an intermediate compound (5) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 67%.

[0040] The obtained intermediate compound (5) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.6 mmol of Target structure 2 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 81%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 668.84; Measured value m/z, 668.24. Elemental analysis (EA): Calculated value C, 87.99; H, 5.43; N, 4.19; Measured value C, 87.84; H, 5.26; N, 4.01.

Embodiment 3

[0041] The synthesis of Target structure 3 of the oxygen heterocyclic compound is shown in process formula 11:

##STR00073##

[0042] In Embodiment 3, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 3 of the oxygen heterocyclic compound provided by Embodiment 3 is as follows:

[0043] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3.3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (6) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.95 mmol of an intermediate compound (7) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 65%.

[0044] The obtained intermediate compound (7) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.7 mmol of Target structure 3 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 85%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 784.35; Measured value m/z, 784.12. Elemental analysis (EA): Calculated value C, 88.74; H, 5.65; N, 3.57; Measured value C, 88.56; H, 5.37; N, 3.89.

Embodiment 4

[0045] The synthesis of Target structure 4 of the oxygen heterocyclic compound is shown in process formula 12:

##STR00074##

[0046] In Embodiment 4, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 4 of the oxygen heterocyclic compound provided by Embodiment 4 is as follows:

[0047] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3.3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (8) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.95 mmol of an intermediate compound (9) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 65%.

[0048] The obtained intermediate compound (9) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.7 mmol of Target structure 4 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 85%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 784.35; Measured value m/z, 784.12. Elemental analysis (EA): Calculated value C, 88.74; H, 5.65; N, 3.57; Measured value C, 88.56; H, 5.37; N, 3.89.

Embodiment 5

[0049] The synthesis of Target structure 5 of the oxygen heterocyclic compound is shown in process formula 13:

##STR00075##

[0050] In Embodiment 5, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 5 of the oxygen heterocyclic compound provided by Embodiment 5 is as follows:

[0051] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3.3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (10) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.8 mmol of an intermediate compound (11) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 60%.

[0052] The obtained intermediate compound (11) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.4 mmol of Target structure 5 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 80%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 667.27; Measured value m/z, 667.31. Elemental analysis (EA): Calculated value C, 88.26; H, 5.14; N, 4.20; Measured value C, 88.31; H, 5.21; N, 4.19.

Embodiment 6

[0053] The synthesis of Target structure 6 of the oxygen heterocyclic compound is shown in process formula 14:

##STR00076##

[0054] In Embodiment 6, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 6 of the oxygen heterocyclic compound provided by Embodiment 6 is as follows:

[0055] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3.3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (12) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 2.2 mmol of an intermediate compound (13) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 72%.

[0056] The obtained intermediate compound (13) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.6 mmol of Target structure 6 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 74%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 744.31; Measured value m/z, 744.31. Elemental analysis (EA): Calculated value C, 88.68; H, 5.41; N, 3.76; Measured value C, 88.52; H, 5.29; N, 3.87.

Embodiment 7

[0057] The synthesis of Target structure 7 of the oxygen heterocyclic compound is shown in process formula 15:

##STR00077##

[0058] In Embodiment 7, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 7 of the oxygen heterocyclic compound provided by Embodiment 7 is as follows:

[0059] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3.3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (14) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 2.4 mmol of an intermediate compound (15) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 79%.

[0060] The obtained intermediate compound (15) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.5 mmol of Target structure 7 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 65%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 784.35; Measured value m/z, 784.13. Elemental analysis (EA): Calculated value C, 88.74; H, 5.65; N, 3.57; Measured value C, 88.69; H, 5.37; N, 3.48.

Embodiment 8

[0061] The synthesis of Target structure 8 of the oxygen heterocyclic compound is shown in process formula 16:

##STR00078##

[0062] In Embodiment 8, the step of producing the previous product-compound (2) can be similar to the step of producing the previous product-compound (2) in Embodiment 1. The preparation method of Target structure 8 of the oxygen heterocyclic compound provided by Embodiment 8 is as follows:

[0063] The product of the previous step-compound (2) (3 mmol), magnesium (Mg, 3.3 mmol), and one grain of 12 were added into a 250 mL two-necked flask, and then 10 mL of THF solvent was added for water and oxygen removal under argon atmosphere; the mixture was stirred until the iodine fades, and reacts for 0.5 hours. Next, compound (16) (3.2 mmol) was dissolved in 50 mL of THF solvent for removing water and oxygen, and then the mixed solution was introduced into the mixed solution prepared in the previous step under argon, and reacts for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 2.1 mmol of an intermediate compound (17) was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 70%.

[0064] The obtained intermediate compound (17) was added into 100 mL of acetonitrile, and 2.5 mmol of boron tribromide was added to the mixture, and stirred for 12 hours. The product was dissolved in dichloromethane (300 mL) and saturated NH.sub.4Cl (200 mL) was added in the mixture. By extraction of dichloromethane, the organic phase was dried by anhydrous sodium sulfate and then subject to column separation after concentration. 1.5 mmol of Target structure 7 was obtained by using 200-300 meshes silica gel as a stationary phase and dichloromethane as an eluent, and the yield is 65%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 733.96; Measured value m/z, 733.79. Elemental analysis (EA): Calculated value C, 90.01; H, 5.91; N, 1.91; Measured value C, 89.87; H, 6.05; N, 1.88.

Embodiment 9

[0065] Target structure 9 is shown in formula 17. Refer to the synthesis of target structure 1 for the synthesis path of target structure 9. The yield of target structure 9 is 65%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 577.73; Measured value m/z, 577.35. Elemental analysis (EA): Calculated value C, 89.40; H, 5.41; N, 2.42; Measured value C, 89.24; H,5.32; N, 2.59.

##STR00079##

[0066] Embodiment 10

[0067] Target structure 10 is shown in formula 18. Refer to the synthesis of target structure 1 for the synthesis path of target structure 10. The yield of target structure 10 is 71%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 617.79; Measured value m/z, 617.54. Elemental analysis (EA): Calculated value C, 89.43; H, 5.71; N, 2.27; Measured value C, 89.21; H,5.85; N, 2.19.

##STR00080##

Embodiment 11

[0068] Target structure 11 is shown in formula 19. Refer to the synthesis of target structure 1 for the synthesis path of target structure 11. The yield of target structure 11 is 74%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): Calculated value m/z, 693.89; Measured value m/z, 693.77. Elemental analysis (EA): Calculated value C, 89.43; H, 5.71; N, 2.27; Measured value C, 89.21; H,5.85; N, 2.19.

##STR00081##

Testing and Experimental Verification

[0069] After testing and experimental verification, the energy levels of the oxygen heterocyclic compound of target structure 1-11 mentioned above are shown in Table 1 below.

TABLE-US-00001 TABLE 1 oxygen heterocyclic compound Eg (eV) HOMO (eV) T1 (eV) Target structure 1 3.34 −5.45 2.89 Target structure 2 3.26 −5.31 2.75 Target structure 3 3.22 −5.35 2.78 Target structure 4 3.21 −5.37 2.84 Target structure 5 3.38 −5.32 2.91 Target structure 6 3.27 −5.40 2.88 Target structure 7 3.56 −5.35 2.79 Target structure 8 3.28 −5.43 2.91 Target structure 9 3.19 −5.45 2.88 Target structure 10 3.40 −5.43 2.85 Target structure 11 3.25 −5.47 2.79

[0070] An electronic device provided by one embodiment of the present disclosure is produced according to the method known in the art. The electronic device is for example an electroluminescent device, specifically comprising an ITO layer, a HAT-CN layer (e.g. 5 nm of thickness), an organic material layer comprising the oxygen heterocyclic compound having any of above target structures (e.g. 30 nm of thickness), a Firpic:B3PyPB layer (12%, 10 nm), a TPBi layer (e.g. 40 nm of thickness), a LiF layer (e.g. 2 nm of thickness), and a Al layer (e.g. 100 nm of thickness). After testing and experimental verification, for each of the oxygen heterocyclic compounds as shown in above target structures 1-11, performance data of the electroluminescent device having the organic material layer comprising the oxygen heterocyclic compound of the target structure is shown in below Table 2.

TABLE-US-00002 TABLE 2 Highest Organic material efficiency layer Voltage (v) (cd/A) Target structure 1 3.2 19.9 Target structure 2 3.3 30.2 Target structure 3 3.2 24.5 Target structure 4 3.4 29.8 Target structure 5 3.3 31.7 Target structure 6 3.1 27.7 Target structure 7 3.4 29.5 Target structure 8 3.5 27.3 Target structure 9 3.7 25.4 Target structure 10 3.9 22.5 Target structure 11 3.8 27.1

[0071] In an oxygen heterocyclic compound, an application thereof, and an electronic device using the same according to the embodiments of the present disclosure, the oxygen heterocyclic compound includes an aromatic amine portion and an oxygen heterocyclic portion, wherein the aromatic amine portion may effectively promote the hole injection and transport performance of the organic material so as to improve the balance between holes and electrons in the organic light-emitting diode to achieve lower voltages and higher efficiencies. In addition, the oxygen heterocyclic portion is conducive to the formation of molten evaporation materials, which is conducive to the stability of mass production evaporation. This type of material can achieve high-efficiency electroluminescent device preparation, which can be used in the manufacture of display devices.

[0072] In summary, although the present invention has been described with preferred embodiments thereof, the present invention is not limited thereto. It is understood that many changes and modifications to the described embodiments can be carried out by the skilled person in the art without departing from the scope and the spirit of the invention that is intended to be limited only by the appended claims.