Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11538996-B2
Application number	US-201916562496-A
Country	US
Kind code	B2
Filing date	Sep 6, 2019
Priority date	Feb 23, 2016
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

The present invention relates to a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.

First claim

The invention claimed is:

1. A compound of formula (Int-1),

where the following applies to the symbols used:
V is CR or N, with the proviso that there are maximum three N per 6-membered-ring, or two adjacent groups V (V—V or V═V) stand for a group of the formula (V-1) or (V-2),

in which the dashed bonds indicate the linking to the spirobifluorene skeleton;
E is a divalent bridge selected from N(R 0 ), B(R 0 ), O, C(R 0 ) 2 , Si(R 0 ) 2 , C═NR 0 , C═C(R 0 ) 2 , S, S═O, SO 2 , P(R 0 ) and P(═O)R 0 ;
X 2 is Cl, Br, I, trifluoromethanesulfonate (CF 3 SO 3 —), tosylate (CH 3 C 6 H 4 SO 3 —) or mesylate (CH 3 SO 3 —);
Ar L is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
R 0 , R, R 2 are selected on each occurrence, identically or differently, from the group consisting of H, D, F, CHO, CN, C(═O)Ar 3 , P(═O)(Ar 3 ) 2 , S(═O)Ar 3 , S(═O) 2 Ar 3 , N(Ar 3 ) 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups may be replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and where one or more H atoms may be replaced by D, F or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 3 , and an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 3 , where two adjacent substituents R 0 , two adjacent substituents R or two adjacent substituents R 2 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R 3 ;
R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CHO, CN, C(═O)Ar 3 , P(═O)(Ar 3 ) 2 , S(═O)Ar 3 , S(═O)Ar 3 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups may be replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and where one or more H atoms may be replaced by D, F or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 3 , and an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 3 , where two adjacent substituents R 1 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R 3 ;
R 3 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CHO, CN, C(═O)Ar 3 , P(═O)(Ar 3 ) 2 , S(═O)Ar 3 , S(═O)Ar 3 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, P(═O)(R 4 ), SO, SO2, O, S or CONR4 and where one or more H atoms may be replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R4, and an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R4, where two adjacent substituents R3 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R 4 ;
R 4 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where one or more non-adjacent CH 2 groups may be replaced by SO, SO 2 , O, S and where one or more H atoms may be replaced by D or F, and aromatic or heteroaromatic ring system having 5 to 24 C atoms;
Ar 3 is selected, identically or differently on each occurrence, from the group consisting of an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 4 ;
n is 1, 2, or 3;
X 2 is Cl, Br, I, trifluoromethanesulfonate (CF 3 SO 3 —), tosylate (CH 3 C 6 H 4 SO 3 —) or mesylate (CH 3 SO 3 —);
X 3 is Cl, Br, I or —B(OR B ) 2 ; with the proviso that one of the group X 1 or X 3 must stand for —B(OR B ) 2 but not both groups stand for —B(OR B ) 2 at the same time.

2. The compound according to claim 1 , characterized in that X 2 is Br, Cl or I.

3. The compound according to claim 1 , selected from formulae (Int-2) to (Int-9),

where the symbols have the same meaning as defined in claim 1 .

4. The compound according to claim 1 , selected from the compounds of formulae (Int-2-1) to (Int-2-8),

where the symbols have the same meaning as in claim 1 .

5. The compound according to claim 1 , selected from the compounds of formulae (Int-2-1-1) to (Int-2-8-1),

where X 2 has the same meaning as in claim 1 .

6. A compound of formula (1-1) or (1-2),

where the symbols V, R 1 have the same meaning as in claim 1 ,
Ar 1 , Ar 2 are, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 ; Ar 1 and Ar 2 here may be connected via a single bond or a divalent bridge selected from —N(R 2 )—, —O—, —S—, —C(R 2 ) 2 —, —C(R 2 ) 2 —C(R 2 ) 2 —, —Si(R 2 ) 2 — and —B(R 2 )—; and
where m is 0, 1, 2, 3 or 4.

7. The compound according to claim 6 , selected from the compounds of formulae (1-1-1) and (1-2-1),

8. The compound according to claim 6 , selected from the compounds of formula (1-1-1a) and (1-2-1a),

9. The compound according to claim 6 , wherein Ar 1 and Ar 2 are selected, identically or differently on each occurrence from the groups of the following formulae (A-1) to (A-48),

Assignees

• Merck Patent Gmbh

Inventors

• Voges Frank
• Mujica-Fernaud Teresa
• Montenegro Elvira

Classifications

• C07C25/22

  with condensed rings · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07C25/18

  Polycyclic aromatic halogenated hydrocarbons · CPC title

• C07D411/12

  linked by a chain containing hetero atoms as chain links · CPC title