Organic el material-containing solution, method for forming organic el thin film, organic el device comprising organic el thin film, and method for manufacturing organic el display panel

1. An organic electroluminescent material-containing solution, comprising:

an organic electroluminescent material;

a solvent, and

a viscosity control reagent, the viscosity control reagent is selected from the group consisting of propanediol, 1,2-butanediol and a mixture thereof;

wherein the organic electroluminescent material at least comprises a host and a dopant,

the host is an anthracene derivative having a molecular weight of 4000 or less, the anthracene derivative being represented by a formula (2) or a formula (4) as follows,

the dopant is a styrylamine derivative represented by any one of formulae (d-1) to (d-11) below, and

the solvent is a cyclic ketone compound represented by a formula (1) as follows, the host of 0.5 mass % or more being soluble in the solvent,

wherein A represents a substituted or unsubstituted cyclic hydrocarbon group having 5 to 10 members or a substituted or unsubstituted group for forming a nitrogen-containing heterocycle having 5 to 10 members,

wherein formula (2) is

wherein Ar represents an unsubstituted fused aromatic group having 10 to 50 carbon atoms forming the aromatic ring;

Ar′ represents an unsubstituted aromatic group having 6 to 50 carbon atoms forming the aromatic ring;

X 3 represents an unsubstituted aromatic group having 6 to 50 carbon atoms forming the aromatic ring, unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms forming the aromatic ring, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkoxy group having 1 to 50 carbon atoms, an unsubstituted aralkyl group having 6 to 50 carbon atoms, an unsubstituted aryloxy group having 5 to 50 carbon atoms, an unsubstituted arylthio group having 5 to 50 carbon atoms, an unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen group, a cyano group, a nitro group or a hydroxyl group;

a and b are 0 and c is an integer of 0 to 4, a plurality of X 3 being allowed to be mutually the same or different when c is 2 or more;

n is an integer from 1 to 3; and

m is 0 or 1,

wherein formula (4) is

wherein Ar 1 and Ar 2 each independently represent an unsubstituted aromatic ring group having 6 to 50 carbon atoms forming the aromatic ring; m and n are each integers of 1 to 4, Ar 1 and Ar 2 are mutually different when: m and n are both equal to 1; and positions at which Ar 1 and Ar 2 are respectively bonded to benzene rings are symmetric, m and n being mutually different when m or n is an integer of 2 to 4;

R 1 to R 8 represent a hydrogen atom, and

R 9 and R 10 each independently represent a hydrogen atom, an unsubstituted aromatic group having 6 to 50 carbon atoms forming the aromatic ring, an unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms forming the aromatic ring, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group, an unsubstituted alkoxy group having 1 to 50 carbon atoms, an unsubstituted aralkyl group having 6 to 50 carbon atoms, an unsubstituted aryloxy group having 5 to 50 atoms forming the ring, an unsubstituted arylthio group having 5 to 50 atoms forming the ring, an unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an unsubstituted silyl group, a carboxyl group, a halogen group, a cyano group, a nitro group or a hydroxyl group; and

wherein formulae (d-1) to (d-11) are

2. A method of forming organic electroluminescent thin film(s), comprising: using the organic electroluminescent material-containing solution according to claim 1 ; and forming thin film(s) of the organic electroluminescent material.

3. The method of forming organic electroluminescent thin film(s) according to claim 2 , further comprising:

ejecting the organic electroluminescent material-containing solution by inkjet method; and

forming film(s) of the organic electroluminescent material by volatilizing the solvent from the ejected organic electroluminescent material-containing solution.

4. A method of manufacturing an organic electroluminescence display panel provided with a first pixel emitting light of a first color and a second pixel emitting light of a second color that is different from the first color, comprising:

preparing an organic electroluminescent material-containing solution for use as a first solution for forming an emitting layer of the first pixel; and

preparing an organic electroluminescent material-containing solution for use as a second solution for forming an emitting layer of the second pixel, wherein

the organic electroluminescent material-containing solution prepared as the first solution comprises the organic electroluminescent material-containing solution according to claim 1 ,

the organic electroluminescent material-containing solution prepared as the second solution comprises an organic electroluminescent material-containing solution, comprising:

an organic electroluminescent material;

a solvent, and

a viscosity control reagent, the viscosity control reagent is selected from the group consisting of propanediol, 1,2-butanediol and a mixture thereof;

wherein the organic electroluminescent material at least comprises a host and a dopant,

the host is a naphthacene derivative represented by a formula (5) as follows,

wherein A, B, C and D each represent a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms or a substituted or unsubstituted fused aromatic group having 10 to 20 carbon atoms, A, B, C and D being allowed to be mutually the same or different,

the dopant is a styrylamine derivative represented by any one of formulae (d-1) to (d-11) below,

the solvent of the first solution and the solvent of the second solution are the same, and

wherein the formulae (d-1) to (d-11) are

5. An organic electroluminescent material-containing solution, comprising:

an organic electroluminescent material;

a solvent, and

a viscosity control reagent, the viscosity control reagent is selected from the group consisting of propanediol, 1,2-butanediol and a mixture thereof;

wherein the organic electroluminescent material at least comprises a host and a dopant,

the host is an anthracene derivative having a molecular weight of 4000 or less, the anthracene derivative being represented by a formula (2) or a formula (4) as follows,

the dopant is an arylamine represented by a formula (8) as follows,

wherein Ar 7 to Ar 9 each represent a substituted or unsubstituted aryl group having 5 to 40 carbon atoms forming the aromatic ring; and

q′ is an integer of 1 to 4, and

the solvent is a cyclic ketone compound represented by a formula (1) as follows, the host of 0.5 mass % or more being soluble in the solvent,

wherein A represents a substituted or unsubstituted cyclic hydrocarbon group having 5 to 10 members or a substituted or unsubstituted group for forming a nitrogen-containing heterocycle having 5 to 10 members,

wherein formula (2) is

wherein Ar represents an unsubstituted fused aromatic group having 10 to 50 carbon atoms forming the aromatic ring;

Ar′ represents an unsubstituted aromatic group having 6 to 50 carbon atoms forming the aromatic ring;

X 3 represents an unsubstituted aromatic group having 6 to 50 carbon atoms forming the aromatic ring, unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms forming the aromatic ring, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkoxy group having 1 to 50 carbon atoms, an unsubstituted aralkyl group having 6 to 50 carbon atoms, an unsubstituted aryloxy group having 5 to 50 carbon atoms, an unsubstituted arylthio group having 5 to 50 carbon atoms, an unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen group, a cyano group, a nitro group or a hydroxyl group;

a and b are 0 and c is an integer of 0 to 4, a plurality of X 3 being allowed to be mutually the same or different when c is 2 or more;

n is an integer from 1 to 3; and

m is 0 or 1,

wherein formula (4) is

wherein Ar 1 and Ar 2 each independently represent an unsubstituted aromatic ring group having 6 to 50 carbon atoms forming the aromatic ring; m and n are each integers of 1 to 4, Ar 1 and Ar 2 are mutually different when: m and n are both equal to 1; and positions at which Ar 1 and Ar 2 are respectively bonded to benzene rings are symmetric, m and n being mutually different when m or n is an integer of 2 to 4;

R 1 to R 8 represent a hydrogen atom, and

R 9 and R 10 each independently represent a hydrogen atom, an unsubstituted aromatic group having 6 to 50 carbon atoms forming the aromatic ring, an unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms forming the aromatic ring, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group, an unsubstituted alkoxy group having 1 to 50 carbon atoms, an unsubstituted aralkyl group having 6 to 50 carbon atoms, an unsubstituted aryloxy group having 5 to 50 atoms forming the ring, an unsubstituted arylthio group having 5 to 50 atoms forming the ring, an unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an unsubstituted silyl group, a carboxyl group, a halogen group, a cyano group, a nitro group or a hydroxyl group.

6. The organic electroluminescent material-containing solution of claim 1 , wherein the anthracene derivative is represented by formula (2).

7. The organic electroluminescent material-containing solution of claim 1 , wherein the anthracene derivative is represented by formula (4).

8. The organic electroluminescent material-containing solution of claim 1 , wherein the cyclic ketone compound represented by a formula (1) is a substituted or unsubstituted cyclic hydrocarbon group having 5 to 10 members selected from the group consisting of cyclohexanone, methyl cyclohexanone, dimethyl cyclohexanone, trimethyl cyclohexanone, ethyl cyclohexanone, n-propyl cyclohexanone, isopropyl cyclohexanone, n-butyl cyclohexanone, isobutyl cyclohexanone, cyclohexyl cyclohexanone, 2-acetyl cyclohexanone, 2-methyl cyclohexanone, 3-methyl cyclohexanone, 4-methyl cyclohexanone, 2-cyclohexyl cyclohexanone, 2-(1-cyclohexenyl)cyclohexanone, 2,5-dimethyl cyclohexanone, 3,4-dimethyl cyclohexanone, 3,5-dimethyl cyclohexanone, 4-ethyl cyclohexanone, pulegone, menthone, 4-pentyl cyclohexanone, 2-propyl cyclohexanone, 3,3,5-trimethyl cyclohexanone, and thujone.

9. The organic electroluminescent material-containing solution of claim 1 , wherein the cyclic ketone compound represented by a formula (1) is a substituted or unsubstituted cyclic hydrocarbon group having 5 to 10 members selected from the group consisting of cyclopentanone, methyl cyclopentanone, dimethyl cyclopentanone, trimethyl cyclopentanone, ethyl cyclopentanone, n-propyl cyclopentanone, isopropyl cyclopentanone, n-butyl cyclopentanone, isobutyl cyclopentanone, and cyclohexyl cyclopentanone.

10. The organic electroluminescent material-containing solution of claim 1 , wherein the cyclic ketone compound represented by a formula (1) is a substituted or unsubstituted cyclic hydrocarbon group having 5 to 10 members selected from the group consisting of cycloheptanone, methyl cycloheptanone, dimethyl cycloheptanone, trimethyl cycloheptanone, ethyl cycloheptanone, n-propyl cycloheptanone, isopropyl cycloheptanone, n-butyl cycloheptanone, isobutyl cycloheptanone, and cyclohexyl cycloheptanone.

11. The organic electroluminescent material-containing solution of claim 1 , wherein the cyclic ketone compound represented by a formula (1) is a nitrogen-containing heterocycle having 5 to 10 members selected from the group consisting of caprolactam, N-methyl caprolactam, 1,3-dimethyl-2-imidazolidine, 2-pyrrolidone, 1-acetyl-2-pyrrolidone, 1-butyl-2-pyrrolidone, 2-piperidone, and 1,5-dimethyl-2-piperidone.

12. The organic electroluminescent material-containing solution of claim 1 , wherein the cyclic ketone compound represented by a formula (1) is N-methyl pyrrolidone.