KR-102964726-B1 - Polymer, composition for organic electroluminescent devices, composition for forming a hole transport layer or a hole injection layer, organic electroluminescent device, organic EL display device and organic EL lighting

Abstract

The present invention provides a polymer having high hole injection transport capacity and high durability, a composition for an organic electroluminescent device containing the polymer, and an organic electroluminescent device having high brightness and a long driving life. A polymer containing a repeating unit represented by the following formula ( 1 ). G is an aromatic hydrocarbon group that may have a substituent, or an N atom. Ar1 is an aromatic hydrocarbon group that may have a substituent. Ar2 , Ar3 , and Ar4 are groups selected from an aromatic hydrocarbon group that may have a substituent, an aromatic complex ring group that may have a substituent, or an aromatic hydrocarbon group that may have a substituent and an aromatic complex ring group that may have a substituent, which are connected in multiple numbers directly or through a linker. X and Y are C atoms or N atoms. The C atoms may have a substituent. "-*" is a bonding site with G.

Inventors

• 리 얀쥔
• 아베 도모히로
• 가지야마 요시코

Assignees

• 미쯔비시 케미컬 주식회사

Dates

Publication Date

20260513

Application Date

20201209

Priority Date

20191216

Claims (16)

1. A polymer containing repeating units represented by the following formula (1). In Equation (1), G represents an N atom. Ar2 represents a divalent group in which two or more groups selected from a divalent aromatic hydrocarbon group that may have substituents, a divalent aromatic complex ring group that may have substituents, or a divalent aromatic hydrocarbon group that may have substituents and a divalent aromatic complex ring group that may have substituents are connected directly or through a linker. A is a structure containing a specific 6-membered complex ring having a nitrogen atom, represented by Equation (1)-2. In formula (1)-2, Ar 1 represents a group in which two or more divalent aromatic hydrocarbon groups that may have substituents are connected. Ar3 and Ar4 each represent a univalent group in which two or more groups selected from an aromatic hydrocarbon group that may have substituents, an aromatic complex ring group that may have substituents, or an aromatic hydrocarbon group that may have substituents and an aromatic complex ring group that may have substituents are connected directly or through a linker. X and Y each independently represent a C atom or an N atom. If X or Y is a C atom, it may have a substituent. "-*" is the part that combines with G in equation (1).
2. In Article 1, A polymer in which the repeating unit represented by the above formula (1) is a repeating unit represented by any of the following formulas (2)-1 to (2)-3. Among Equations (2)-1 to (2)-3, A is the same as A in Equation (1) above. Q represents -C(R 5 )(R 6 )-, -N(R 7 )- or -C(R 11 )(R 12 )-C(R 13 )(R 14 )-. R1 to R4 each independently represent an alkyl group that may have a substituent, an alkoxy group that may have a substituent, or an aralkyl group that may have a substituent. R 5 to R 7 and R 11 to R 14 each independently represent an alkyl group that may have a substituent, an alkoxy group that may have a substituent, an aralkyl group that may have a substituent, or an aromatic hydrocarbon group that may have a substituent. a and b are each independently integers from 0 to 4. c1 to c5 are each independently integers from 0 to 3. However, at least one of c3 and c5 is 1 or greater. d1 to d4 are each independently integers from 1 to 4. If there are multiple R1 , R2 , R3 , and R4 among the repeating units, R1 , R2 , R3 , and R4 may be the same or different.
3. In Article 1, In addition, a polymer containing a repeating unit represented by any one of (3)-1 to (3)-3 below. In formulas (3)-1 to (3)-3, Ar7 represents an aromatic hydrocarbon group that may have substituents or an aromatic complex ring group that may have substituents, excluding a group containing a specific six-membered complex aromatic ring having a nitrogen atom of structure A represented by formula (1)-2. Q represents -C(R 5 )(R 6 )-, -N(R 7 )- or -C(R 11 )(R 12 )-C(R 13 )(R 14 )-. R1 to R4 each independently represent an alkyl group that may have a substituent, an alkoxy group that may have a substituent, or an aralkyl group that may have a substituent. R 5 to R 7 and R 11 to R 14 each independently represent an alkyl group that may have a substituent, an alkoxy group that may have a substituent, an aralkyl group that may have a substituent, or an aromatic hydrocarbon group that may have a substituent. a and b are each independently integers from 0 to 4. c1 to c5 are each independently integers from 0 to 3. However, at least one of c3 and c5 is an integer greater than or equal to 1. d1 to d4 are each independently integers from 1 to 4. If there are multiple R1 , R2 , R3 , and R4 among the repeating units, R1 , R2 , R3 , and R4 may be the same or different.
4. In Article 1, The above polymer is a polymer having a crosslinking group as a substituent.
5. In Article 1, A polymer having a weight average molecular weight (Mw) of 10,000 or more and a dispersion (Mw/Mn) of 3.5 or less.
6. In Article 1, A polymer comprising at least one benzene ring connected at the 1,3 position, in which Ar 1 of the above formula (1)-2.
7. A composition for an organic electroluminescent device containing a polymer described in any one of claims 1 to 6.
8. A composition for forming a hole transport layer or a hole injection layer containing a polymer described in any one of claims 1 to 6.
9. A method for manufacturing an organic electroluminescent device having an anode, a cathode, and an organic layer between the anode and the cathode on a substrate, comprising a film deposition step in which at least one layer of the organic layer is formed by a wet film deposition method using a composition for an organic electroluminescent device described in claim 7, wherein the organic layer is at least one of a hole injection layer and a hole transport layer.
10. In Article 9, A method for manufacturing an organic electroluminescent device comprising a hole injection layer, a hole transport layer, and a light-emitting layer between the anode and the cathode, wherein the organic layer formed in the film formation step is the hole injection layer or the hole transport layer.
11. An organic electroluminescent device comprising a layer containing a polymer described in any one of claims 1 to 6, or a polymer crosslinked with the polymer.
12. An organic EL display device having an organic electroluminescent element as described in claim 11.
13. Organic EL lighting having an organic electroluminescent element as described in claim 11.
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Description

Polymer, composition for organic electroluminescent devices, composition for forming a hole transport layer or a hole injection layer, organic electroluminescent device, organic EL display device and organic EL lighting The present invention relates to polymers. More specifically, the present invention relates to polymers useful as charge transport materials for organic electroluminescent devices. The present invention also relates to a composition for an organic electroluminescent device containing said polymer, a composition for forming a hole transport layer or a hole injection layer, an organic electroluminescent device comprising a layer formed using said composition, a method for manufacturing said organic electroluminescent devices, and an organic EL display device and an organic EL lighting device having said organic electroluminescent device. Methods for forming an organic layer in an organic electroluminescent device include vacuum deposition and wet deposition. Because vacuum deposition facilitates stacking, it has the advantage of improving charge injection from the anode and/or cathode and facilitating the blocking of excitons in the emissive layer. On the other hand, the wet film deposition method does not require a vacuum process, making it easy to expand to a large area, and has advantages such as being able to easily form a layer containing multiple materials with various functions by using a coating solution that mixes multiple materials with various functions. However, since the wet film deposition method is difficult to stack, the driving stability is inferior compared to devices made by vacuum deposition, and the current situation is that, with the exception of some, it has not reached a practical level. In order to perform stacking by wet film deposition, a charge-transporting polymer having crosslinkable groups is desired, and such development is being carried out. For example, Patent Documents 1 to 3 disclose an organic electroluminescent device stacked by wet film deposition containing a polymer having specific repeating units. Patent documents 4 and 5 disclose a hole injection transport material having a structure in which a fluorene ring or a carbazole ring and a phenylene ring without a substituent are bonded to the main chain of a polymer. Patent Document 6 describes that, in a polymer having repeating units of sp3 hybridized quaternary carbon C4 and phenylene, it is preferable to include non-conjugated units in the main chain. Patent Document 6 discloses a side chain structure in which a triazine ring is connected to the main chain via an alkylene group. Patent Document 7 discloses a compound in which a triazine group having a substituent is connected to a polymer having repeating units comprising silicon atoms and a carbazole ring in the main chain, wherein an aryl group is interposed at the 9th position of the carbazole ring. Patent document 8 discloses a polymer having a pyridine structure in the side chain of a polymer having an arylamine structure. FIG. 1 is a schematic cross-sectional view showing an example of the structure of an organic electroluminescent device of the present invention. Hereinafter, embodiments of a polymer according to one embodiment of the present invention, a composition for an organic electroluminescent device containing the polymer according to another embodiment, a composition for forming a hole transport layer or a hole injection layer, an organic electroluminescent device including a layer formed using the composition, a method for manufacturing the same, and an organic EL display device and an organic EL lighting having the organic electroluminescent device are described in detail. The following description is an example (representative example) of an embodiment of the present invention, and the present invention is not limited to these contents unless it exceeds the gist thereof. 〔polymer〕 A polymer that is one embodiment of the present invention is a polymer containing repeating units represented by the following formula (1). [Chemical Formula 4] In formula (1), G represents an aromatic hydrocarbon group that may have a substituent, or an N atom. Ar2 represents a divalent group in which two or more groups selected from a divalent aromatic hydrocarbon group that may have substituents, a divalent aromatic complex ring group that may have substituents, or a divalent aromatic hydrocarbon group that may have substituents and a divalent aromatic complex ring group that may have substituents are connected directly or through a linker. A is a structure containing a specific 6-membered complex ring having a nitrogen atom, represented by Equation (1)-2. In formula (1)-2, Ar 1 represents a divalent aromatic hydrocarbon group that may have a substituent. Ar3 and Ar4 each represent a univalent group in which two or more groups selected from an aromatic hydrocarbon group that may have substituents, an aromatic complex ring group that may have substituents