Organic electroluminescent element and manufacturing method thereof, and phosphorus-containing organic compound and manufacturing method thereof

1. A manufacturing method of an organic electroluminescent element including an anode, a cathode and a plurality of organic compound layers sandwiched between the anode and cathode, the process comprising the steps of:

forming a hole-transporting layer using an organic compound insoluble in alcohols; and

forming an electron-transporting layer directly on the hole-transporting layer by a wet method using as an electron transporting layer material a phosphorus-containing organic compound dissolved in an alcohol;

wherein the phosphorus-containing organic compound is represented by the general formula (1):

wherein Ar 1 -Ar 3 , the same or different from each other, represent an aromatic ring residue optionally containing a substituent.

2. The manufacturing method of an organic electroluminescent element according to claim 1 , wherein the alcohol is a linear or branched C 1 -C 6 aliphatic alcohol.

3. The manufacturing method of claim 1 , wherein the atomic ring residue is:

a monocyclic aromatic ring or heterocycle chosen from a benzene ring, a thiophene ring, a triazine ring, a furan ring, a pyrazine ring or a pyridine ring;

a condensed polycyclic aromatic ring or heterocycle chosen from a naphthalene ring, an anthracene ring, a thieno[3,2-b]thiophene ring, a phenanthrene ring, a fluorene ring or a furo[3,2-b]furan ring;

a ring-aggregated aromatic ring or heterocycle chosen from a biphenyl ring, a terphenyl ring, a bithiophene ring or a bifuran ring; and

an aromatic ring or heterocycle chosen from a acridine ring, an isoquinoline ring, an indole ring, a carbazole ring, a carboline ring, a quinoline ring, a dibenzofuran furan ring, a cinnoline ring, a thionaphthene ring, a 1,10-phenanthroline ring, a phenothiazine ring, a purine ring, a benzofuran ring or a silol ring.

4. The method of claim 1 , wherein Ar 1 -Ar 3 are independently optionally substituted by one or more of an alkyl group, an alkoxy group, a halogen atom, cyano group, nitro group, amino group, an aryl group and a diarylphosphinyl group.

5. The method of claim 3 , wherein the atomic ring residue is independently optionally substituted by one or more of an alkyl group, an alkoxy group, a halogen atom, cyano group, nitro group, amino group, an aryl group and a diarylphosphinyl group.

6. A manufacturing method of an organic electroluminescent element including an anode, a cathode and a plurality of organic compound layers sandwiched between the anode and cathode, the process comprising the steps of:

forming a hole-transporting layer using an organic compound insoluble in alcohols; and

forming an electron-transporting layer directly on the hole-transporting layer by a wet method using as an electron transporting layer material a phosphorus-containing organic compound dissolved in an alcohol;

wherein the phosphorus-containing organic compound is represented by the general formula (2):

wherein Ar 1 -Ar 6 , the same or different from each other, represent an aromatic ring residue optionally containing a substituent; and Ar 7 -Ar 9 , the same or different from each other, represent an arylene group optionally containing a substituent.

7. The manufacturing method of an organic electroluminescent element according to claim 6 , wherein the alcohol is a linear or branched C 1 -C 6 aliphatic alcohol.

8. A manufacturing method of an organic electroluminescent element including an anode, a cathode and a plurality of organic compound layers sandwiched between the anode and cathode, the process comprising the steps of:

forming a hole-transporting layer using an organic compound insoluble in alcohols; and

forming an electron-transporting layer directly on the hole-transporting layer by a wet method using as an electron transporting layer material a phosphorus-containing organic compound dissolved in an alcohol;

wherein the phosphorus-containing organic compound is represented by the general formula (3):

wherein R 1 or R 2 , the same or different from each other, represents a hydrogen atom, an alkyl group, a halogen atom, cyano group, nitro group, amino group, an aryl group or a diarylphosphinyl group, and R 1 and R 2 can form, together with a carbon atom of a benzene ring to which they are linked, a substituted or unsubstituted aromatic ring; and n is 1 or 2.

9. The manufacturing method of an organic electroluminescent element according to claim 8 , wherein the alcohol is a linear or branched C 1 -C 6 aliphatic alcohol.