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CN-122029150-A - Material for electronic devices

CN122029150ACN 122029150 ACN122029150 ACN 122029150ACN-122029150-A

Abstract

The present invention relates to a compound according to formula (I), its use in an electronic device, a method for its preparation and an electronic device comprising a compound according to formula (I).

Inventors

  • ELVIRA MONTENEGRO
  • Ruwen Ringer

Assignees

  • 默克专利有限公司

Dates

Publication Date
20260512
Application Date
20241016
Priority Date
20231017

Claims (15)

  1. 1. A compound according to the following formula (I) The compound of formula (I), Wherein the following applies to the variables present in the formula: Z 1 is selected identically or differently on each occurrence from CR 1 and N; Z 11 、Z 12 、Z 13 、Z 14 is each identically or differently selected from CR 11 and N if the bond introduced into the ring comprising Z 11 、Z 12 、Z 13 、Z 14 is not connected to Z 11 、Z 12 、Z 13 、Z 14 , and Z 11 、Z 12 、Z 14 is C if the bond introduced into the ring comprising Z 11 、Z 12 、Z 14 is connected to Z 11 、Z 12 、Z 14 ; Z 15 is selected identically or differently on each occurrence from CR 11 and N; Y is selected from O, S and NR 2 ; Ar 1 is selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl and tetrabiphenyl, each of which is substituted by a radical R 31 , and fluorenyl which is linked in one of its 1 to 4 positions and is substituted by a radical R 3 ; R 1 is selected identically or differently on each occurrence from H、D、F、C(=O)R 4 、CN、Si(R 4 ) 3 、N(R 4 ) 2 、P(=O)(R 4 ) 2 、OR 4 、S(=O)R 4 、S(=O) 2 R 4 、 straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, alkenyl or alkynyl groups having 2 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where two or more radicals R 1 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are substituted by radicals R 4 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 4 C=CR 4 -、-C≡C-、Si(R 4 ) 2 、C=O、C=NR 4 、-C(=O)O-、-C(=O)NR 4 -、NR 4 、P(=O)(R 4 )、-O-、-S-、SO or SO 2 ; R 11 is selected identically or differently on each occurrence from H、D、F、C(=O)R 4 、CN、Si(R 4 ) 3 、N(R 4 ) 2 、P(=O)(R 4 ) 2 、OR 4 、S(=O)R 4 、S(=O) 2 R 4 、 straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, alkenyl or alkynyl groups having 2 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where two or more radicals R 11 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are substituted by radicals R 4 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 4 C=CR 4 -、-C≡C-、Si(R 4 ) 2 、C=O、C=NR 4 、-C(=O)O-、-C(=O)NR 4 -、NR 4 、P(=O)(R 4 )、-O-、-S-、SO or SO 2 ; R 2 is selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl radical having from 1 to 20C atoms, a branched or cyclic alkyl radical having from 3 to 20C atoms, an aromatic ring system having from 6 to 40 aromatic ring atoms and a heteroaromatic ring system having from 5 to 40 aromatic ring atoms, wherein the alkyl radical and the aromatic ring system and heteroaromatic ring system are substituted by the radical R 4 ; R 3 is selected identically or differently on each occurrence from H、D、F、C(=O)R 4 、CN、Si(R 4 ) 3 、N(R 4 ) 2 、P(=O)(R 4 ) 2 、OR 4 、S(=O)R 4 、S(=O) 2 R 4 、 straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, alkenyl or alkynyl groups having 2 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where two or more radicals R 3 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are substituted by radicals R 4 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 4 C=CR 4 -、-C≡C-、Si(R 4 ) 2 、C=O、C=NR 4 、-C(=O)O-、-C(=O)NR 4 -、NR 4 、P(=O)(R 4 )、-O-、-S-、SO or SO 2 ; R 31 is selected identically or differently on each occurrence from H、D、F、C(=O)R 4 、CN、Si(R 4 ) 3 、N(R 4 ) 2 、P(=O)(R 4 ) 2 、OR 4 、S(=O)R 4 、S(=O) 2 R 4 、 straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, alkenyl or alkynyl groups having 2 to 20C atoms, where two or more radicals R 31 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups are substituted by radicals R 4 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 4 C=CR 4 -、-C≡C-、Si(R 4 ) 2 、C=O、C=NR 4 、-C(=O)O-、-C(=O)NR 4 -、NR 4 、P(=O)(R 4 )、-O-、-S-、SO or SO 2 ; r 4 is selected identically or differently on each occurrence from H、D、F、C(=O)R 5 、CN、Si(R 5 ) 3 、N(R 5 ) 2 、P(=O)(R 5 ) 2 、OR 5 、S(=O)R 5 、S(=O) 2 R 5 、 straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, alkenyl or alkynyl groups having 2 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where two or more radicals R 4 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are substituted by radicals R 5 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 5 C=CR 5 -、-C≡C-、Si(R 5 ) 2 、C=O、C=NR 5 、-C(=O)O-、-C(=O)NR 5 -、NR 5 、P(=O)(R 5 )、-O-、-S-、SO or SO 2 ; R 5 is selected identically or differently on each occurrence from H, D, F, CN, an alkyl group having from 1 to 20C atoms, an aromatic ring system having from 6 to 40C atoms and a heteroaromatic ring system having from 5 to 40 aromatic ring atoms, where two or more radicals R 5 can be connected to one another to form a ring, and where the alkyl group, aromatic ring system and heteroaromatic ring system can be substituted by one or more radicals selected from F and CN; Wherein the bond introduced into the ring comprising Z 11 、Z 12 、Z 13 and Z 14 is attached to one of Z 11 、Z 12 and Z 14 , and Wherein, if a bond introduced into a ring containing Z 11 、Z 12 、Z 13 and Z 14 is linked to Z 14 , one of the two groups Ar 1 is selected from fluorenyl substituted with a group R 3 and the other of the two groups Ar 1 is selected from phenyl, biphenyl, terphenyl and tetrabiphenyl each substituted with R 31 , and Wherein, if Y is O or S, the bond incorporated into the ring comprising Z 11 、Z 12 、Z 13 and Z 14 is attached to one of Z 11 and Z 14 .
  2. 2. The compound according to claim 1, characterized in that it corresponds to one of the following formulae: Wherein in each of the formulae (I-B-1), (I-B-2), (I-B-3), one of the two groups Ar 1 is selected from fluorenyl substituted with the group R 3 , and the other of the two groups Ar 1 is selected from phenyl, biphenyl, terphenyl, and tetrabiphenyl each substituted with R 31 ; And wherein p is 3, q is 5, m is 3 and n is 4; and wherein the other variable groups are the same as defined in claim 1; wherein formulae (I-A-a), (I-A-b) and (I-A-c) are preferred, and formula (I-A-a) is most preferred.
  3. 3. Compound according to claim 1 or 2, characterized in that Y is selected from O and S, preferably O.
  4. 4. A compound according to one or more of claims 1 to 3, characterized in that the groups Ar 1 are identically or differently selected from phenyl, biphenyl, terphenyl and tetrabiphenyl each having no substituents and fluorenyl which is attached at one of its 1-to 4-positions and is substituted by a group R 3 .
  5. 5. The compound according to one or more of claims 1 to 4, characterized in that one of a) and b) is suitable, a) both groups Ar 1 are biphenyl groups without substituents, and b) both groups Ar 1 are fluorenyl groups which are linked in one of their 1-to 4-positions and are substituted by a group R 3 .
  6. 6. Compound according to one or more of claims 1 to 5, characterized in that the bond introduced into the ring comprising Z 11 、Z 12 、Z 13 and Z 14 is linked to one of Z 11 and Z 14 , and preferably in that said bond is linked to Z 11 .
  7. 7. Compound according to one or more of claims 1 to 6, characterized in that R 1 is identically or differently selected from H, D, a linear alkyl radical having 1 to 20C atoms, a branched or cyclic alkyl radical having 3 to 20C atoms, an aromatic ring system having 6 to 40 aromatic ring atoms substituted by the radical R 4 and a heteroaromatic ring system having 5 to 40 aromatic ring atoms substituted by the radical R 4 .
  8. 8. Compound according to one or more of claims 1 to 7, characterized in that R 11 is identically or differently selected from H, D and aromatic ring systems with 6 to 40 aromatic ring atoms substituted by the radical R 4 and heteroaromatic ring systems with 5 to 40 aromatic ring atoms substituted by the radical R 4 .
  9. 9. Compound according to one or more of claims 1 to 8, characterized in that R 31 is H.
  10. 10. Compound according to one or more of claims 1 to 9, characterized in that it satisfies the following conditions: the compounds correspond to the formula (I), preferably to one of the formulae (I-A-a), (I-A-b) and (I-A-c), most preferably to the formula (I-A-a), and Y is selected from O and S, preferably Y is O, and -Z 1 is CR 1 , and Z 11 、Z 12 、Z 13 、Z 14 is CR 11 if the bond introduced into the ring comprising Z 11 、Z 12 、Z 13 、Z 14 is not attached to Z 11 、Z 12 、Z 13 、Z 14 and Z 11 、Z 12 、Z 14 is C if the bond introduced into the ring comprising Z 11 、Z 12 、Z 14 is attached to Z 11 、Z 12 、Z 14 , and -Z 15 is CR 11 , and Ar 1 is identically or differently selected from phenyl, biphenyl, terphenyl and tetrabiphenyl, each of which has no substituents, and fluorenyl which is linked in one of its 1 to 4 positions and is substituted by a radical R 3 , and R 1 is selected from H, D and aromatic ring systems substituted by the radical R 4 having 6 to 40 aromatic ring atoms and heteroaromatic ring systems substituted by the radical R 4 having 5 to 40 aromatic ring atoms, and R 11 is identical or different from H, D and an aromatic ring system substituted by a radical R 4 and having 6 to 40 aromatic ring atoms, a heteroaromatic ring system substituted by a radical R 4 and having 5 to 40 aromatic ring atoms, and R 2 is selected from the group consisting of aromatic ring systems having 6 to 40 aromatic ring atoms, substituted by the radical R 4 , and R 3 is identical or different from H, D, F, a linear alkyl radical having 1 to 20C atoms, a branched or cyclic alkyl radical having 3 to 20C atoms, an aromatic ring system having 6 to 40 aromatic ring atoms which is substituted by the radical R 4 and a heteroaromatic ring system having 5 to 40 aromatic ring atoms which is substituted by the radical R 4 , and R 31 is identically or differently selected from H, D, F, a linear alkyl radical having 1 to 20C atoms which is substituted by a radical R 4 , a branched or cyclic alkyl radical having 3 to 20C atoms which is substituted by a radical R 4 , and R 4 is identically or differently selected from H, D, F, CN, si (R 5 ) 3 、N(R 5 ) 2 , straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where the alkyl and alkoxy groups and the aromatic and heteroaromatic ring systems are substituted by a group R 5 , and R 5 is identical or different from H, D, F, CN, an alkyl group having 1 to 20C atoms, an aromatic ring system having 6 to 40C atoms and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, wherein the alkyl group, the aromatic ring system and the heteroaromatic ring system may be substituted by one or more groups selected from F and CN.
  11. 11. A process for the preparation of a compound according to one or more of claims 1 to 10, characterized in that in a first step a biphenyl derivative having two reactive groups is reacted with a dibenzofuranyl, dibenzothienyl or carbazolyl derivative in a Suzuki coupling reaction, wherein one of the two reactive groups is present in the 3-position of the biphenyl derivative and the other is present in the 4-position of the biphenyl derivative, the dibenzofuranyl, dibenzothienyl or carbazolyl derivative having a reactive group on one of its aromatic cores, wherein the reactive group in the 4-position is reacted in the coupling reaction.
  12. 12. A formulation comprising at least one compound according to one or more of claims 1 to 10 and at least one solvent.
  13. 13. An electronic device comprising at least one compound according to one or more of claims 1 to 10.
  14. 14. An electronic device according to claim 13, characterized in that the electronic device is an organic electroluminescent device and comprises an anode, a cathode and at least one light-emitting layer, and in that the compound is present in a hole-transporting layer or in the light-emitting layer of the device.
  15. 15. Use of a compound according to one or more of claims 1 to 10 in an electronic device.

Description

Material for electronic devices The present application relates to an aromatic amine compound containing a heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl and carbazolyl groups, and a biphenyl-containing moiety having an amine substituent bonded thereto. The compounds are suitable for use in electronic devices. An electronic device in the context of the present application is understood to mean a so-called organic electronic device, which comprises an organic semiconductor material as functional material. More specifically, these are understood to mean OLEDs (organic electroluminescent devices). The term OLED is understood to mean an electronic device having one or more layers comprising an organic compound and emitting light upon application of a voltage. The general principles of the construction and function of OLEDs are known to those skilled in the art. In electronic devices, especially OLEDs, there is a great interest in improving performance data. In these respects, it has not been possible to find any fully satisfactory solution. The light-emitting layer and the layer having a hole transporting function have a great influence on performance data of the electronic device. Novel compounds for use in these layers, in particular hole-transporting compounds and compounds which can be used as hole-transporting host materials in light-emitting layers, in particular for phosphorescent emitters, are also sought. For this purpose, in particular, compounds having a high glass transition temperature, high stability and high hole conductivity are sought. The high stability of the compounds is a prerequisite for achieving a long lifetime of the electronic device. Furthermore, there is a need to find improved compounds whose use in electronic devices results in performance data of the devices, in particular compounds which result in high efficiency, long lifetime and low operating voltages. In the prior art, triarylamine compounds, such as spirobifluorene and fluorenamine in particular, are known as hole transporting materials and hole transporting host materials for electronic devices. Also known are heteroaryl substituted benzidines as disclosed in WO2023/025971, WO2019/206292, CN110577510 and CN 116478115. Nevertheless, there is still room for improvement regarding the above-described characteristics. It has now been found that aromatic amines of the following formula (I) have excellent suitability for use in electronic devices, characterized in that they comprise heteroaryl-substituted benzidine moieties. They are particularly suitable for use in OLEDs, even more particularly, as hole-transporting materials therein and as hole-transporting host materials, in particular for phosphorescent emitters. These compounds result in high lifetime, high efficiency and low operating voltage of the device. Further preferably, the compounds are found to have a high glass transition temperature, high stability, low sublimation temperature, good solubility, good synthesis accessibility and high hole conductivity. The present application therefore relates to a compound according to the formula (I) The compound of formula (I), Wherein the following applies to the variables present in the formula: Z 1 is selected identically or differently on each occurrence from CR 1 and N; Z 11、Z12、Z13、Z14 is each identically or differently selected from CR 11 and N if the bond introduced into the ring comprising Z 11、Z12、Z13、Z14 is not connected to Z 11、Z12、Z13、Z14, and Z 11、Z12、Z14 is C if the bond introduced into the ring comprising Z 11、Z12、Z14 is connected to Z 11、Z12、Z14; Z 15 is selected identically or differently on each occurrence from CR 11 and N; Y is selected from O, S and NR 2; Ar 1 is selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl and tetrabiphenyl, each of which is substituted by a radical R 31, and fluorenyl which is linked in one of its 1 to 4 positions and is substituted by a radical R 3; R 1 is selected identically or differently on each occurrence from H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4、 straight-chain alkyl or alkoxy groups having 1 to 20C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20C atoms, alkenyl or alkynyl groups having 2 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where two or more radicals R 1 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are substituted by radicals R 4, and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-O-、-S-、SO or SO 2; R 11 is selected identically or differently on each occurrence from H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4、 strai