Carbazole derivatives

Patent metadata

Field	Value
Publication number	US-10964894-B2
Application number	US-201816480129-A
Country	US
Kind code	B2
Filing date	Jan 22, 2018
Priority date	Jan 25, 2017
Publication date	Mar 30, 2021
Grant date	Mar 30, 2021

Abstract

The present invention relates to carbazole derivatives, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.

First claim

The invention claimed is:

1. A compound comprising at least one structure of the formula (I)

where the symbols used are as follows:
X is the same or different at each instance and is N or CR 1 , or C if the indolo group is bonded to X;
W 1 is O, S, C(R 1 ) 2 , P(═O)Ar or Si(R 1 ) 2 ;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 2 ) 2 , C(═O)Ar 1 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , B(OR 2 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems; at the same time, two or more R 1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals;
Ar 1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R 2 radicals; at the same time, two Ar 1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom may also be joined together via a bridge by a single bond or a bridge selected from the group consisting of B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR 3 ) 2 , NO 2 , C(═O)R 3 , CR 3 ═C(R 3 ) 2 , C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , P(R 3 ) 2 , B(R 3 ) 2 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent 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═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or a combination of these systems; at the same time, two or more R 2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
R 3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more R 3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

2. The compound according to claim 1 , comprising at least one structure of the formula (IIa), (IIb), (IIc), (IId), (IIe) or MO

where the symbols Ar, W 1 and X used have the definition given in claim 1 .

3. The compound according to claim 1 , comprising at least one structure of the formula (IIIa), (IIIb), (IIIc), (IIId), (IIIe) or (IIIf)

where the symbols R 1 , Ar, W 1 and X have the definition given in claim 1 and m is 0, 1, 2, 3 or 4.

4. The compound according to claim 1 , comprising at least one structure of the formula (IVa), (IVb), (IVc), (IVd), (IVe) or (IVf)

where the symbols R 1 , Ar, W 1 and X have the definition given in claim 1 and o is 0, 1 or 2.

5. The compound according to claim 1 , comprising at least one structure of the formula (Va), (Vb), (Vc), (Vd), (Ve) or (Vf)

where the symbols R 1 , Ar, W 1 and X used have the definition given in claim 1 and I is 0, 1, 2, 3, 4, 5 or 6.

6. The compound according to claim 1 , comprising at least one structure of the formula (VIa), (VIb), (VIc), (VId), (VIe) or (VIf)

where the symbols R 1 , Ar, W 1 and X have the definition given in claim 1 , l is 0, 1, 2, 3, 4, 5 or 6, m is 0, 1, 2, 3 or 4 and o is 0, 1 or 2.

7. The compound according to claim 1 , wherein the Ar group comprises or constitutes a hole transport group.

8. The compound according to claim 1 , wherein the Ar group comprises or constitutes an electron transport group.

9. The compound according to claim 8 , wherein the Ar group is a group that can be represented by the formula (QL)
Q-L 1 -  Formula (QL)

in which L 1 represents a bond or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals, and Q is an electron transport group, where
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 2 ) 2 , C(═O)Ar 1 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , B(OR 2 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromat

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir
• Ludemann Aurélie
• Joosten Dominik
• Grossmann Tobias
• Kroeber Jonas

Classifications

• C07F9/65685

  the ring phosphorus atom being part of a phosphine oxide or thioxide · CPC title

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C07D495/16

  Peri-condensed systems · CPC title

• C07D495/06

  Peri-condensed systems · CPC title

• C07D491/22

  in which the condensed system contains four or more hetero rings · CPC title