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JP-7855516-B2 - Materials for electronic devices

JP7855516B2JP 7855516 B2JP7855516 B2JP 7855516B2JP-7855516-B2

Inventors

  • モンテネグロ、エルビラ
  • ムジカ－フェルナウド、テレサ
  • トゥフィン、ラッヘル
  • ブルーイン、ニコラス

Assignees

  • メルク パテント ゲーエムベーハー

Dates

Publication Date
20260508
Application Date
20210204
Priority Date
20200206

Claims (18)

  1. Formula (I) or (II) (In the formula, the following applies to the variable group: G is given by equation (G-1) or (G-2) It is a base by, In the formulas, the dotted line represents a bond to the remainder of formula (I) or (II), where the bond is at one of the positions marked with a # in formulas (G-1) and (G-2), and the group R1 is bonded to all free positions on the aromatic rings of formulas (G-1) and (G- 2 ); L1 is an aromatic ring system having 6 to 40 aromatic ring atoms substituted with the group R2 , or a heteroaromatic ring system having 5 to 40 aromatic ring atoms substituted with the group R2; Ar 1 is selected from aromatic ring systems having 6 to 40 aromatic ring atoms substituted with the group R 3 , either identically or differently in each occurrence, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted with the group R 3 ; Ar 2 is selected from aromatic ring systems having 6 to 40 aromatic ring atoms substituted with the group R 3 , either identically or differently in each occurrence, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted with the group R 3 ; E is a single bond or a divalent group selected from C( R4 ) 2 , Si( R4 ) 2 , NR4 , O, and S; T is a single bond or a divalent group selected from C( R4 ) 2 , Si( R4 ) 2 , NR4 , O, and S, identical or different in each occurrence; n is either 0 or 1, where n=0, in which case group L1 does not exist, and group G and the N atom are directly linked; R0 is selected from H, D, F, Cl, Br, I, C(=O) R5 , CN, Si( R5 ) 3 , N( R5 ) 2 , P(=O)( R5 ) 2 , OR5 , S(=O) R5 , S(=O)2R5 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two radicals R0 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R 5 is substituted, and one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may be replaced in each case 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 SO2 ; R1 is selected from H, D, F, Cl, Br, I, C(=O) R5 , CN, Si( R5 ) 3 , N( R5 ) 2 , P(=O)( R5 ) 2 , OR5 , S(=O) R5 , S(=O)2R5 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two or more radicals R1 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R 5 is substituted, and one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may be replaced in each case 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 SO2 ; R2 is selected from H, D, F, Cl, Br, I, C(=O) R5 , CN, Si( R5 ) 3 , N( R5 ) 2 , P(=O)( R5 ) 2 , OR5 , S(=O) R5 , S(=O)2R5 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two or more radicals R2 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R2 5 is substituted, and one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may be replaced in each case 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 SO2 ; R 3 is selected from H, D, F, Cl, Br, I, 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) 2R 5 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two or more radicals R 3 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R 5 is substituted, and one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may be replaced in each case 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 SO2 ; R 4 is selected from H, D, F, Cl, Br, I, 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) 2R 5 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two or more radicals R 4 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R 5 is substituted, and one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may be replaced in each case 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 SO2 ; R 5 is selected from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(=O)(R 6 ) 2 , OR 6 , S(=O)R 6 , S(=O) 2R 6 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two or more radicals R 5 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R Substituted by 6 , one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may be replaced in each case by -R6 C= CR6- , -C≡C-, Si( R6 ) 2 , C=O, C= NR6 , -C(=O)O-, -C(=O) NR6- , NR6 , P(=O)( R6 ), -O-, -S-, SO or SO2 ; R 6 is selected from H, D, F, Cl, Br, I, CN, an alkyl group having 1 to 20 carbon atoms, an aromatic ring system having 6 to 40 carbon atoms, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, identically or differently in each occurrence; where two or more radicals R 6 may be linked to each other to form a ring; the alkyl group, aromatic ring system and heteroaromatic ring system may be substituted with one or more radicals selected from F and CN; Here, in formula (I), each of the three groups -Ar1 , -Ar1 , and -[ L1 ] n -G contains at least one D atom bonded to an aromatic or heteroaromatic ring; here, in formula (II), each of the three groups -Ar2 , -Ar2 , and -[ L1 ] n -G contains at least one D atom bonded to an aromatic or heteroaromatic ring. A compound of [unclear].
  2. The compound according to claim 1, characterized by being a monoamine.
  3. The compound according to claim 1 or 2 , characterized in that G is a group according to formula (G-1).
  4. ( G -1) is given by equation (G-1-1-1) (In the formulas, the dotted lines represent bonds to the remainder of formula (I) or (II), where group R1 is bonded to all free positions on the aromatic ring of formula (G-1-1-1).) The compound according to claim 3 , characterized by conforming to the following.
  5. The compound according to claim 4 , characterized in that R1 is D.
  6. The compound according to any one of claims 1 to 5 , characterized in that L1 is selected from a divalent group derived from benzene, biphenyl, naphthalene, and fluorene, wherein L1 is substituted with a radical R2 .
  7. A compound according to any one of claims 1 to 6 , characterized in that n is 0.
  8. The compound according to any one of claims 1 to 7, wherein group Ar 1 is selected, either identically or differently, from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, particularly 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl, phenyl substituted with naphthyl, phenyl substituted with fluorenyl, phenyl substituted with spirobifluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophenyl, phenyl substituted with carbazolyl, phenyl substituted with pyridyl, phenyl substituted with pyrimidyl, and phenyl substituted with triazinyl , wherein each of the groups is substituted with a radical R 3 .
  9. The basis of equation (II) However, the following formula: (In the equation, the dotted line represents the connection to the remainder of equation (II).) A compound according to any one of claims 1 to 8 , characterized by being selected from the above.
  10. A compound according to any one of claims 1 to 9 , characterized in that R1 is D, or R1 is completely deuterated, and/or R2 is D.
  11. Equations (I) and (II) are given by equations (I-1-1) and (II-1-1). (In the formula, the variable group is as defined in claim 1 , and all free positions on spirobifluorene are substituted with group R1 .) A compound according to any one of claims 1 to 10 , characterized by conforming to the above.
  12. The compound according to any one of claims 1 to 11 , characterized in that R3 is D.
  13. The compound according to any one of claims 1 to 12 , characterized in that the compound is completely deuterated.
  14. A material characterized in that a compound described in any one of claims 1 to 13 is present in the material with a purity of more than 90% by weight.
  15. A preparation comprising at least one compound according to any one of claims 1 to 13 and at least one solvent.
  16. An electronic device comprising at least one compound as described in any one of claims 1 to 13 .
  17. The electronic device according to claim 16, wherein the electronic device is an organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer, and at least one organic layer of the device, which is a hole transport layer, an electron blocking layer, or a hole injection layer, comprises the at least one compound.
  18. Use of the compound according to any one of claims 1 to 13 in an electronic device.

Description

This application relates to amine compounds suitable for use in electronic devices, particularly organic electroluminescent devices (OLEDs). In the context of this application, "electronic device" is understood to mean a so-called organic electronic device containing an organic semiconductor material as a functional material. More specifically, "electronic device" is understood to mean an OLED. The use of organic compounds as functional materials in OLEDs is common knowledge in the prior art. Generally, the term OLED is understood to mean an electronic device having one or more layers containing organic compounds that emits light when a voltage is applied. In electronic devices, particularly OLEDs, there is strong interest in improving performance data, especially lifespan, efficiency, and operating voltage. However, no completely satisfactory solution has yet been found in these areas. Layers with hole transport properties, such as hole injection layers, hole transport layers, electron blocking layers, and light-emitting layers, significantly impact the performance data of electronic devices. New materials with hole transport characteristics are continuously being sought for use in these layers. In the course of this invention, it has been discovered that amine compounds having a spirobifluorene group, a group derived from spirobifluorene, or a fluorene group, and being completely or partially deuterated in the manner described in detail below, are very well suited for use as materials with hole transport properties, particularly as materials for hole transport layers, electron blocking layers, and/or light-emitting layers, and more specifically for use in hole transport layers and/or electron blocking layers. In this context, the electron blocking layer is understood to be a layer that is directly adjacent to the light-emitting layer on the anode side and functions to prevent electrons present in the light-emitting layer from entering the hole transport layer of the OLED. When used in electronic devices, particularly OLEDs, these compounds yield excellent results in terms of device lifespan, operating voltage, and quantum efficiency. The compounds also feature very good hole conduction properties, very good electron blocking properties, a high glass transition temperature, high oxidation stability, good solubility, high thermal stability, and a low sublimation temperature. Therefore, this application is based on formula (I) or (II). (In the formula, the following applies to the variable group: G is given by equation (G-1) or (G-2) It is a base by, In the formulas, the dotted line represents a bond to the remainder of formula (I) or (II), where the dotted line represents a bond at one of the positions marked with a # in formulas (G-1) and (G-2), where the group R1 is bonded to all free positions on the aromatic rings of formulas (G-1) and (G-2); In formulas (G-1) and (G-2), each of the benzene rings is a ring Aa to Ai: (In the formula, the positions marked with an asterisk (*) are the attachment points to the remainder of the base in formula (G-1) or (G-2), W1 represents C( R1 ) 2 , Si( R1 ) 2 , N( R1 ), S, O, Se, or C=O; V 1 represents CR 1 or N; R11 to R18 are defined as R1 . It is arbitrarily replaced with one of the following: L1 is an aromatic ring system having 6 to 40 aromatic ring atoms substituted with the group R2 , or a heteroaromatic ring system having 5 to 40 aromatic ring atoms substituted with the group R2 ; Ar 1 is selected from aromatic ring systems having 6 to 40 aromatic ring atoms substituted with the group R 3 , either identically or differently in each occurrence, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted with the group R 3 ; Ar 2 is selected from aromatic ring systems having 6 to 40 aromatic ring atoms substituted with the group R 3 , either identically or differently in each occurrence, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted with the group R 3 ; E is a single bond or a divalent group selected from C( R4 ) 2 , Si( R4 ) 2 , NR4 , O, and S; T is a single bond or a divalent group selected from C( R4 ) 2 , Si( R4 ) 2 , NR4 , O, and S, identical or different in each occurrence; n is either 0 or 1, where n=0, in which case group L1 does not exist, and group G and the N atom are directly linked; R0 is selected from H, D, F, Cl, Br, I, C(=O) R5 , CN, Si( R5 ) 3 , N( R5 ) 2 , P(=O)( R5 ) 2 , OR5 , S(=O) R5 , S(=O)2R5 , a linear alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, where two radicals R0 may be linked to each other to form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups, and the aromatic and heteroaromatic ring systems are radicals R 5 is s