Hexacyclic heteroaromatic compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-11535619-B2
Application number	US-201816615267-A
Country	US
Kind code	B2
Filing date	May 18, 2018
Priority date	May 22, 2017
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

The invention relates to heteroaromatic compounds, particularly for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention and to electronic devices containing same.

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:
Y is the same or different at each instance and is a bond or NR 1 , NAr, O, S, C(R 1 ) 2 , CArR 1 , C(Ar) 2 , Si(Ar) 2 , SiArR 1 or Si(R 1 ) 2 , where at least one Y group is selected from NR 1 , NAr, O, S, C(R 1 ) 2 , CArR 1 , C(Ar) 2 , Si(Ar) 2 , SiArR 1 or Si(R 1 ) 2 ;
X is the same or different at each instance and is N or CR 1 ,
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; at the same time, two Ar radicals bonded to the same carbon atom or silicon atom may also be joined to one another by a single bond or a bridge selected from B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R 1 ), P(R 1 ) and P(═O)R 1 ;
R 1 is the same or different at each instance and is H, D, OH, OR 2 , 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 or alkynyl 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 radicals may form a ring system with one another;
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 nonaromatic R 2 radicals; at the same time, it is possible for two Ar 1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another by a single bond or a bridge selected from 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 1 ) 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 substituents may also form a ring system with one another;
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 which has 5 to 30 aromatic ring atoms and 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, it is also possible for two or more substituents to form a ring system with one another.

2. The compound as claimed in claim 1 , comprising at least one structure of the formula (IIa) or (IIb)

where the symbols Y and X used have the definition given in claim 1 .

3. The compound as claimed in claim 1 , comprising at least one structure of the formula (IIIa), (IIIb), (IVa), (IVb), (Va) or (Vb)

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

4. The compound as claimed in claim 1 , comprising at least one structure of the formula (VIa) or (VIb)

where the symbols R 1 and Y have the definition given in claim 1 , m is the same or different at each instance and is 0, 1, 2, 3 or 4, and n is 0, 1, 2 or 3.

5. The compound as claimed in claim 1 , characterized in that the compound comprises a hole transport group.

6. The compound as claimed in claim 5 , characterized in that the hole transport group comprises a group selected from the formulae (H-1) to (H-3)

where the dotted bond marks the position of attachment and in addition:
Ar 2 , Ar 3 , Ar 4 is in each case independently an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, each of which may be substituted by one or more R 1 radicals,
p is 0 or 1,
Z is C(R 1 ) 2 , Si(R 1 ) 2 , C═O, N—Ar 1 , BR 1 , PR 1 , POR 1 , SO, SOL, Se, O or S, where the symbols Ar 1 and R 1 have the definition given in claim 1 , where the presence of an N—N bond is ruled out, such that, in the case that Y═NAr, the index p=1.

7. The compound as claimed in claim 5 , characterized in that the hole transport group comprises a group selected from the formulae (H-4) to (H-26)

where Y 1 represents O, S, C(R 1 ) 2 or NAr 1 , the dotted bond marks the position of attachment, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is 0, 1, 2, 3 or 4, p is 0 or 1,
R 1 is the same or different at each instance and is H, D, OH, OR 2 , 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 carbo

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C07D471/22 Primary

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

• C07D491/22

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

• C07D498/22

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

• C07D497/22

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

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title