Organic electroluminescent element material, organic electroluminescent element and production method for organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-10840461-B2
Application number	US-201113805154-A
Country	US
Kind code	B2
Filing date	Jun 28, 2011
Priority date	Jun 30, 2010
Publication date	Nov 17, 2020
Grant date	Nov 17, 2020

Abstract

Provided is an organic electroluminescence device material, which, in its production, is free from formation of impurities that worsen the performance of organic EL devices, which, in forming an upper layer by coating, does not cause dissolution mixing or swelling mixing, which forms a film of good quality and which contributes toward improving the performance (high durability, and low driving voltage) of organic EL devices. The organic electroluminescence device material is a siloxane compound having a recurring unit represented by the following general formula (1):

First claim

The invention claimed is:

1. A material for an organic electroluminescence device comprising an acyclic siloxane compound that is end-capped with a trialkysilanol and the remainder of the acyclic siloxane compound consisting of a repeating unit represented by formula (1), a repeating unit represented by —(SiR 11 R 12 O)—, and a repeating unit containing Si H:

wherein R 1 represents an alkyl group or an aryl group,
L 1 represents a divalent linking group having 3 or more carbon atoms,
HL represents a group including two or more of a triarylamine unit,
the content of the —(SiR 11 R 12 O)— unit is at most 80 mol % relative to the total content of the structural unit represented by formula (1),
R 11 and R 12 each independently represent an alkyl group, and
the content of the unit containing Si—H is at most 20 mol % relative to the total of the recurring units represented by formula (1);
wherein at least one of the following conditions is true:
(a) R 11 and R 12 each independently represent an unsubstituted alkyl group; or
(b) Li represents a divalent linking group having 3 or more carbon atoms and at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom.

2. The material for an organic electroluminescence device according to claim 1 , wherein the HL in the formula (1) is represented by formula (2):

wherein each of Ar 1 , Ar 2 and Ar 4 independently represents an arylene group,
each of Ar 3 , Ar 5 and Ar 6 independently represents an aryl group,
Z 2 represents a divalent linking group,
Ar 4 , Ar 5 , Ar 6 and Z 2 may be the same or different from each other if each of Ar 4 , Ar 5 , Ar 6 and Z 2 is plurally present,
n represents a number of Z 2 in each of triarylamine units and n is 0 or 1,
m represents a repeating number of the triarylamine unit and m is an integer of 1 or more,
when m is 2 or more, in the each of the triarylamine units Ar 5 in one of the triarylamine units is bound to Z 2 in the other triarylamine unit,
when n is 0 and m is 1, Ar 2 and Ar 4 are bound to each other via a single bond,
when n is 0 and m is 2 or more, Ar 2 and Ar 4 are bound to each other via a single bond and, in the each of triarylamine units, Ar 4 in one of the triarylamine units is bound to Ar 5 in the other triarylamine unit, and
*2 represents a site to be bound to L 1 in the formula (1).

3. The material for an organic electroluminescence device according to claim 1 , wherein L 1 in the formula (1) is represented by formula (3):

wherein R 2 represents a hydrogen atom or an alkyl group,
T represents a divalent linking group,
W represents an oxygen atom, —NH— or a sulfur atom,
V represents a divalent linking group,
X represents —CH 2 —, an oxygen atom or —NH—,
p represents an integer of 1 to 5,
s represents 0 or 1,
u represents an integer of 0 to 5,
z represents 0 or 1,
T and V may be the same or different from each other if each of T and V is plurally present, provided that any one of T, V and X includes at least one carbon atom,
*3 represents a site to be bound to a silicon atom in the formula (1), and
*4 represents a site to be bound to HL in the formula (1).

4. The material for an organic electroluminescence device according to claim 1 ,
wherein, in the siloxane compound, a ratio of a repeating unit including Si—H to a total of the repeating unit represented by the formula (1) is 0 to 10%.

5. The material for an organic electroluminescence device according to claim 1 ,
wherein the siloxane compound is a 10- to 50-mer of the repeating unit represented by the formula (1).

6. The material for an organic electroluminescence device according to claim 2 , wherein the formula (2) is represented by formula (5):

wherein each of R 51 to R 78 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a silyl group, provided that any one of R 51 to R 55 is bound to L 1 in the formula (1), and
Z 5 represents a single bond or a divalent linking group.

7. The material for an organic electroluminescence device according to claim 2 , wherein the formula (2) is represented by formula (6):

wherein each of R 51 to R 82 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a silyl group, provided that any one of R 51 to R 55 is bound to L 1 in the formula (1), and
Z 6 represents a single bond or a divalent linking group.

8. The material for an organic electroluminescence device according to claim 2 , wherein the formula (2) is represented by formula (7):

wherein each of R 51 to R 82 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a silyl group, provided that any one of R 51 to R 55 is bound to L 1 in the formula (1), and
Z 7 represents a single bond or a divalent linking group.

9. An organic electroluminescence device comprising, on a substrate:
a pair of electrodes including an anode and a cathode;
a plurality of organic layers between the electrodes, wherein at least one of the plurality of organic layers is a light emitting layer and at least one of the plurality of organic layers is between the anode and the light emitting layer and
contains the material for an organic electroluminescence device according to claim 1 .

10. The organic electroluminescence device according to claim 9 ,
wherein the material for an organic electroluminescence device is contained in a hole injection layer.

11. The organic electroluminescence device according to claim 9 ,
wherein the material for an organic electroluminescence device is contained in a hole transport layer.

12. A method for manufacturing the organic electroluminescence device according to claim 9 ,
wherein the layer including the material for an organic electroluminescence device is formed by a wet process.

13. A film comprising the material for an organic electroluminescence device according to claim 1 .

Assignees

• Yonekuta Yasunori
• Takaku Koji
• Hayashi Naoyuki
• Udc Ireland Ltd

Inventors

• Yonekuta Yasunori
• Takaku Koji
• Hayashi Naoyuki

Classifications

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• C08G77/388 Primary

  containing nitrogen · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C08K5/18

  with aromatically bound amino groups · CPC title

• H01L51/006

  Electricity · mapped topic