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CN-122029156-A - Material for electronic devices

CN122029156ACN 122029156 ACN122029156 ACN 122029156ACN-122029156-A

Abstract

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

Inventors

  • Ruwen Ringer
  • ELVIRA MONTENEGRO

Assignees

  • 默克专利有限公司

Dates

Publication Date
20260512
Application Date
20241016
Priority Date
20231017

Claims (16)

  1. 1. A compound according to 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 1 、CR 11 and N if the bond introduced into the ring containing Z 11 、Z 12 、Z 13 、Z 14 is not linked to Z 11 、Z 12 、Z 13 、Z 14 , and Z 11 、Z 12 、Z 13 、Z 14 is C if the bond introduced into the ring containing Z 11 、Z 12 、Z 13 、Z 14 is linked to Z 11 、Z 12 、Z 13 、Z 14 ; Z 15 、Z 16 、Z 17 、Z 18 is selected identically or differently on each occurrence from CR 1 、CR 11 and N; Y is selected from O or S; Ar 1 is selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl and tetrabiphenyl, wherein phenyl, biphenyl, terphenyl and tetrabiphenyl are each substituted by a radical R 21 , and fluorenyl substituted by a radical R 2 , which fluorenyl is connected in one of its 1 to 4 positions; R 1 is selected identically or differently on each occurrence from ：H,D,F,C(=O)R 3 ,CN,Si(R 3 ) 3 ,N(R 3 ) 2 ,P(=O)(R 3 ) 2 ,OR 3 ,S(=O)R 3 ,S(=O) 2 R 3 , 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 of the radicals R 1 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are substituted by radicals R 3 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 3 C=CR 3 -、-C≡C-、Si(R 3 ) 2 、C=O、C=NR 3 、-C(=O)O-、-C(=O)NR 3 -、NR 3 、P(=O)(R 3 )、-O-、-S-、SO or SO 2 ; R 11 is selected identically or differently on each occurrence from an aromatic ring system having 6 to 24 aromatic ring atoms and a heteroaromatic ring system having 5 to 24 aromatic ring atoms, wherein the aromatic ring system and the heteroaromatic ring system are each substituted by a group R 3 ; R 2 is selected identically or differently on each occurrence from H,D,F,C(=O)R 3 ,CN,Si(R 3 ) 3 ,N(R 3 ) 2 ,P(=O)(R 3 ) 2 ,OR 3 ,S(=O)R 3 ,S(=O) 2 R 3 , 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 of the radicals R 2 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are substituted by radicals R 3 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R 3 C=CR 3 -、-C≡C-、Si(R 3 ) 2 、C=O、C=NR 3 、-C(=O)O-、-C(=O)NR 3 -、NR 3 、P(=O)(R 3 )、-O-、-S-、SO or SO 2 ; r 21 is selected identically or differently on each occurrence from a linear alkyl or alkoxy radical H,D,F,C(=O)R 3 ,CN,Si(R 3 ) 3 ,N(R 3 ) 2 ,P(=O)(R 3 ) 2 ,OR 3 ,S(=O)R 3 ,S(=O) 2 R 3 , having from 1 to 20C atoms, a branched or cyclic alkyl or alkoxy radical having from 3 to 20C atoms, an alkenyl or alkynyl radical having from 2 to 20C atoms, where two or more radicals R 21 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl radicals are substituted by radicals R 3 , and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl radicals can in each case be replaced by -R 3 C=CR 3 -、-C≡C-、Si(R 3 ) 2 、C=O、C=NR 3 、-C(=O)O-、-C(=O)NR 3 -、NR 3 、P(=O)(R 3 )、-O-、-S-、SO or SO 2 ; R 3 is selected identically or differently on each occurrence from H,D,F,Cl,Br,I,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 of the radicals R 3 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic 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 4 is selected identically or differently on each occurrence from H, D, F, cl, br, I, CN, an alkyl radical 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 4 can be connected to one another to form a ring, and where the alkyl radical, 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 、Z 13 and Z 14 , and Wherein at least one of Z 11 、Z 12 、Z 13 、Z 14 、Z 15 、Z 16 、Z 17 and Z 18 is CR 11 .
  2. 2. A compound according to claim 1, characterized in that it corresponds to one of the following formulae: Wherein the variable groups are as defined in claim 1, and wherein Y is preferably O, and wherein Z 1 is preferably CR 1 .
  3. 3. A compound according to claim 1, characterized in that exactly one of each formula Z 11 、Z 12 、Z 13 、Z 14 、Z 15 、Z 16 、Z 17 and Z 18 is CR 11 , wherein preferably all other Z 11 、Z 12 、Z 13 、Z 14 、Z 15 、Z 16 、Z 17 and Z 18 are CR 1 .
  4. 4. A compound according to one or more of claims 1 to 3, 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 12 and Z 13 .
  5. 5. Compound according to one or more of claims 1 to 4, characterized in that Y is O.
  6. 6. A compound as claimed in one or more of claims 1 to 5, characterized in that the radicals Ar 1 are chosen identically or differently from phenyl, biphenyl, terphenyl and tetrabiphenyl, each of which carries no substituents, and from fluorenyl substituted by the radical R 2 , the fluorenyl being linked in one of its 1 to 4 positions.
  7. 7. The compound according to one or more of claims 1 to 6, characterized in that one of a) and b) is suitable, a) both groups Ar 1 being biphenyl without substituents and b) both groups Ar 1 being fluorenyl substituted by a group R 3 , the fluorenyl being linked in one of its 1-to 4-positions.
  8. 8. Compound according to one or more of claims 1 to 7, characterized in that R 1 is identically or differently selected from H, D, straight-chain alkyl groups having 1 to 20C atoms, branched or cyclic alkyl groups having 3 to 20C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms substituted by the radical R 3 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted by the radical R 3 , wherein R 1 is preferably selected from H and D, wherein most preferably R 1 is H.
  9. 9. The compound according to one or more of claims 1 to 8, characterized in that R 11 is identically or differently selected from the group consisting of aromatic ring systems substituted with the radical R 3 having from 6 to 24 aromatic ring atoms, most preferably R 11 is selected from the group consisting of phenyl, biphenyl, terphenyl and naphthyl substituted with the radical R 3 .
  10. 10. The compound according to one or more of claims 1 to 9, characterized in that R 2 on the aromatic ring of the fluorenyl group as Ar 1 is identically or differently selected from H, D, F, straight-chain alkyl groups having 1 to 20C atoms and branched or cyclic alkyl groups having 3 to 20C atoms, and R 2 on the bridgehead aliphatic carbon atom of the fluorenyl group as Ar 1 is identically or differently selected from F, straight-chain alkyl groups having 1 to 20C atoms, branched or cyclic alkyl groups having 3 to 20C atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by groups R 3 .
  11. 11. Compound according to one or more of claims 1 to 10, characterized in that it satisfies the following conditions: The compounds correspond to formula (I), preferably to one of the formulae (I-B-a), (I-B-B), (I-C-a) and (I-C-B), and Y is O, and -Z 1 is CR 1 , and Z 11 、Z 12 、Z 13 、Z 14 is each chosen identically or differently from CR 1 and CR 11 if the bond introduced into the ring comprising Z 11 、Z 12 、Z 13 and Z 14 is not linked to Z 11 、Z 12 、Z 13 、Z 14 , and Z 11 、Z 12 、Z 13 、Z 14 is C if the bond introduced into the ring comprising Z 11 、Z 12 、Z 13 、Z 14 is linked to Z 11 、Z 12 、Z 13 、Z 14 , and Z 15 、Z 16 、Z 17 、Z 18 is identically or differently selected from CR 1 and CR 11 , and Exactly one of Z 11 、Z 12 、Z 13 、Z 14 、Z 15 、Z 16 、Z 17 and Z 18 is CR 11 , and Ar 1 is identically or differently selected from phenyl, biphenyl, terphenyl and tetrabiphenyl, each of which carries no substituents, and fluorenyl substituted by a radical R 2 , the fluorenyl being linked in one of its 1 to 4 positions, and R 1 is identically or differently selected from H, D, a straight-chain 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 3 , and a heteroaromatic ring system having 5 to 40 aromatic ring atoms which is substituted by the radical R 3 , and R 11 is identical or different from the group consisting of phenyl, biphenyl, terphenyl and naphthyl substituted by the radical R 3 , where R 3 is identical or different from the group consisting of H, D, F, a linear alkyl radical having from 1 to 20C atoms and a branched or cyclic alkyl radical having from 3 to 20C atoms, and R 2 is identical or different from H, D, F, a straight-chain 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 3 , and a heteroaromatic ring system having 5 to 40 aromatic ring atoms which is substituted by the radical R 3 , and R 3 is identically or differently selected from H, D, F, CN, si (R 4 ) 3 ,N(R 4 ) 2 , straight-chain alkyl or alkoxy radicals having 1 to 20C atoms, branched or cyclic alkyl or alkoxy radicals 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 radicals and the aromatic and heteroaromatic ring systems are substituted by the radical R 4 , and R 4 is identically or differently selected from H, D, F, CN, alkyl groups having 1 to 20C atoms, aromatic ring systems having 6 to 40C atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where the alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more groups selected from F and CN.
  12. 12. A process for the preparation of a compound according to one or more of claims 1 to 11, characterized in that in a first step a biphenyl derivative is reacted with a dibenzofuranyl derivative or a dibenzothiophenyl derivative in a bell-wood coupling reaction, said biphenyl derivative bearing two reactive groups, wherein one of said 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, said dibenzofuranyl derivative or dibenzothiophenyl derivative bearing a reactive group on one of its aromatic cores and bearing an aromatic or heteroaromatic group as substituent, wherein said reactive group in the 4-position is reacted in said coupling reaction.
  13. 13. A formulation comprising at least one compound according to one or more of claims 1 to 11 and at least one solvent.
  14. 14. An electronic device comprising at least one compound according to one or more of claims 1 to 11.
  15. 15. The electronic device according to claim 14, 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 a light-emitting layer of the device.
  16. 16. Use of a compound according to one or more of claims 1 to 11 in an electronic device.

Description

Material for electronic devices The present application relates to aromatic amine compounds containing a heteroaryl group selected from aryl or heteroaryl substituted dibenzofuranyl and aryl or heteroaryl substituted dibenzothiophenyl, 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 comprising an organic semiconductor material as functional material. More particularly, these are understood to mean OLEDs (organic electroluminescent devices). The term OLED is understood to mean an electronic device which has one or more layers comprising organic compounds and emits light when a voltage is applied. 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, no completely satisfactory solution has been found. The light-emitting layer and the layer having a hole transporting function have an important influence on performance data of the electronic device. New compounds for use in these layers, in particular hole-transporting compounds and compounds that can be used as hole-transporting host materials in light-emitting layers, in particular for phosphorescent emitters, are also being sought. For this purpose, in particular, compounds having a high glass transition temperature, high stability and high hole conductivity are being sought. The high stability of the compounds is a prerequisite for achieving long life of the electronic device. There is also a need to find compounds that when used in electronic devices, lead to improvements in the performance data of the devices, especially high efficiency, long lifetime and low operating voltages. Triarylamine compounds, such as spirobifluorene and fluorenamine in particular, are known in the art as hole transporting materials and hole transporting host materials for electronic devices. Also known are heteroaryl substituted benzidines, such as disclosed in WO 2023/025971, WO 2019/206292, CN 110577510 and CN 116478115. However, there is still room for improvement in the above performance. It has now been found that aromatic amines of the following formula (I) are of excellent applicability when used in electronic devices, which aromatic amines are characterized in that they comprise dibenzofuranyl or dibenzothienyl substituted benzidine moieties, wherein the dibenzofuranyl and dibenzothienyl groups are substituted with aromatic or heteroaromatic groups. They are particularly suitable for use in OLEDs and even more particularly for use therein as hole-transporting materials and as hole-transporting host materials, in particular for phosphorescent emitters. These compounds lead to high lifetime, high efficiency and low operating voltage of the device. Also preferably, the compounds found have a high glass transition temperature, high stability, low sublimation temperature, good solubility, good synthesis accessibility and high hole conductivity. At this time, the present application relates to 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、Z12、Z13、Z14 is each identically or differently selected from CR 1、CR11 and N if the bond introduced into the ring containing Z 11、Z12、Z13、Z14 is not linked to Z 11、Z12、Z13、Z14, and Z 11、Z12、Z13、Z14 is C if the bond introduced into the ring containing Z 11、Z12、Z13、Z14 is linked to Z 11、Z12、Z13、Z14; Z 15、Z16、Z17、Z18 is selected identically or differently on each occurrence from CR 1、CR11 and N; Y is selected from O or S; Ar 1 is selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl and tetrabiphenyl, wherein phenyl, biphenyl, terphenyl and tetrabiphenyl are each substituted by a radical R 21, and fluorenyl substituted by a radical R 2, which fluorenyl is connected in one of its 1 to 4 positions; R 1 is selected identically or differently on each occurrence from ：H,D,F,C(=O)R3,CN,Si(R3)3,N(R3)2,P(=O)(R3)2,OR3,S(=O)R3,S(=O)2R3, 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 of the radicals R 1 can be connected to one another to form a ring, where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are substituted by radicals R 3, and where one or more CH 2 groups of the alkyl, alkoxy, alkenyl and alkynyl groups can in each case be replaced by -R3C=CR