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US 10,374,168 B2Granted
Materials for electronic devices
AssigneeMerck Patent GmbH
InventorsJochen Pfister, Frank Voges, Elvira Montenegro, Teresa Mujica-Fernaud
Life of this patent
Estimating the term…
Abstract
The present application relates to heterospirobifluorene compounds, to a process for the preparation thereof, and to electronic devices, in particular organic electroluminescent devices, comprising the heterospirobifluorene derivatives.
Claims23
A compound of the formula (I)
- where the following applies to the symbols and indices occurring:
- A is C;
- Y is N;
- X is on each occurrence, identically or differently, CR1 or N;
- Ar1, Ar2 are on each occurrence, identically or differently, selected from the formula (Ar-2) to (Ar-15) and (Ar-18) to (Ar-66)
- Ar3, Ar4, Ar5, Ar6 on each occurrence, identically or differently, conform to formula (Ar-1),
- which is optionally substituted by one or more radicals R2 on the free positions, and where the bond denoted by * represents the bonding position of the respective group;
- R1, R2 are selected on each occurrence, identically or differently, from H, D, F, C(═O)R3, CF3, OCF3, 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 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C 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 R1 or R2 is optionally linked to one another and may form a ring;
- where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R3;
- and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO or SO2;
- R3 is selected on each occurrence, identically or differently, from H, D, F, C(═O)R4, CF3, OCF3, 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 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C 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 R3 is optionally linked to one another and may form a ring;
- where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R4;
- and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally 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 SO2;
- R4 is selected on each occurrence, identically or differently, from H, D, F, CN, alkyl groups having 1 to 20 C 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 R4 is optionally linked to one another and may form a ring;
- and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems is optionally substituted by F or CN;
- a, b, c, d are on each occurrence, identically or differently, 0 or 1;
- and
- wherein at least one of the indices a, b, c and d is equal to 1.
18 more elements
An oligomer, polymer or dendrimer containing one or more compounds of the formula (I)
- where the following applies to the symbols and indices occurring:
- A is C or Si;
- Y is on each occurrence, identically or differently, N or P;
- X is on each occurrence, identically or differently, CR1 or N;
- Ar1, Ar2 are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2;
- Ar3, Ar4, Ar5, Ar6 are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2;
- R1, R2 are selected on each occurrence, identically or differently, from H, D, F, C(═O)R3, CF3, OCF3, 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 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C 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 R1 or R2 is optionally linked to one another and may form a ring;
- where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R3;
- and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO or SO2;
- R3 is selected on each occurrence, identically or differently, from H, D, F, C(═O)R4, CF3, OCF3, 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 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C 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 R3 is optionally linked to one another and may form a ring;
- where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R4;
- and where one or more CI2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally 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 SO2,
- R4 is selected on each occurrence, identically or differently, from H, D, F, CN, alkyl groups having 1 to 20 C 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 R4 is optionally linked to one another and may form a ring;
- and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems is optionally substituted by F or CN;
- a, b, c, d are on each occurrence, identically or differently, 0 or 1;
- where at least one of the two groups Ar1 and Ar2 is an aromatic ring system having 12 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a heteroaromatic ring system having 12 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2;
- and
- wherein at least one of the indices a, b, c and d is equal to 1,
- where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any position in formula (I) that are substituted by R1 or R2.
19 more elements
A compound of the formula (I)
- where the following applies to the symbols and indices occurring:
- A is C;
- Y is N;
- X is on each occurrence, identically or differently, CR1 or N;
- Ar1, Ar2 are on each occurrence, identically or differently, selected from the formula (Ar-2) to (Ar-15) and (Ar-18) to (Ar-66)
- Ar3, Ar4, Ar5, Ar6 are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2;
- R1, R2 are selected on each occurrence, identically or differently, from H, D, F, C(═O)R3, CF3, OCF3, 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 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C 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 R1 or R2 is optionally linked to one another and may form a ring;
- where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R3;
- and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO or SO2;
- R3 is selected on each occurrence, identically or differently, from H, D, F, C(═O)R4, CF3, OCF3, 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 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C 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 R3 is optionally linked to one another and may form a ring;
- where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteararomatic ring systems may each be substituted by one or more radicals R4;
- and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally 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 SO2;
- R4 is selected on each occurrence, identically or differently, from H, D, F, CN, alkyl groups having 1 to 20 C 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 R4 is optionally linked to one another and may form a ring;
- and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems is optionally substituted by F or CN;
- a, b, c, d are on each occurrence, identically or differently, 0 or 1;
- and
- wherein at least one of the indices a, b, c and d is equal to 1.
17 more elements
Dependencies are inferred from the claim text.