IP Library Patent Application 17775948
Patent Application
App. No. 17/775,948

MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

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Patent No.
US None
App. No.
17/775,948
Abstract

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.

Claims (115)

1 .- 24 . (canceled)

25 . Compound of the formula (1),

where the following applies to the symbols and indices used:

X 1 stands, on each occurrence, identically or differently, for CR 1 or N;

X 2 stands, on each occurrence, identically or differently, for CR 2 or N;

X A stands, on each occurrence, identically or differently, for CR A or N;

Y 1 stands for a single bond or a divalent bridge selected from —C(R Y ) 2 —, —C(R Y ) 2 —C(R Y ) 2 —, —Si(R Y ) 2 —, —O—, —S—, —S(═O) 2 — and —C(═O)—;

Y 2 stands for a divalent bridge selected from —C(R Y ) 2 —, —C(R Y ) 2 —C(R Y ) 2 —, —Si(R Y ) 2 —, —O—, —S—, —S(═O) 2 — and —C(═O)—;

R B stands on each occurrence, identically or differently, for CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, N(R) 2 , Si(R) 3, 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 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 radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, P(═O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals;

R Y , R N stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , N(R) 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 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 radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, P(═O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; where two adjacent substituents R Y may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R′;

R 1 , R 2 , R A stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, P(═O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; where two adjacent radicals selected from R 1 , R 2 , R A may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R;

R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , Si(R′) 3 , B(OR′) 2 , OSO 2 R′, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R′, where in each case one or more non-adjacent CH 2 groups may be replaced by R′C═CR′, C≡C, Si(R′) 2 , Ge(R′) 2 , Sn(R′) 2 , C═O, C═S, C═Se, P(═O)(R′), SO, SO 2 , O, S or CONR′ and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R′, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R′, where two adjacent radicals R may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R′;

Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case also be substituted by one or more radicals R′;

R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case 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, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms.

26 . Compound according to claim 25 , characterized in that it is selected from compounds of formula (2),

where the symbols have the same meaning as in claim 25 .

27 . Compound according to claim 25 , characterized in that it is selected from compounds of formula (3),

where the symbols have the same meaning as in claim 25 .

28 . Compound according to claim 25 , characterized in that R B stands on each occurrence, identically or differently, for a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 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 radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, P(═O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.

29 . Compound according to claim 25 , characterized in that RB stands on each occurrence, identically or differently, for a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D, F, Cl or CN, or an aromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.

30 . Compound according to claim 25 , characterized in that RB is selected on each occurrence, identically or differently,

from branched or cyclic alkyl groups represented by the general following formula (RS-a)

wherein

R 22 , R 23 , R 24 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 , and where two of radicals R 22 , R 23 , R 24 or all radicals R 22 , R 23 , R 24 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R 25 ;

R 25 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms;

with the proviso that at each occurrence at least one of radicals R 22 , R 23 and R 24 is other than H, with the proviso that at each occurrence all of radicals R 22 , R 23 and R 24 together have at least 4 carbon atoms and with the proviso that at each occurrence, if two of radicals R 22 , R 23 , R 24 are H, the remaining radical is not a straight-chain;

or from branched or cyclic alkoxy groups represented by the general following formula

(RS-b)

wherein

R 26 , R 27 , R 28 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 as defined above, and where two of radicals R 26 , R 27 , R 28 or all radicals R 26 , R 27 , R 28 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R 25 as defined above;

with the proviso that at each occurrence only one of radicals R 26 , R 27 and R 28 may be H;

or from aralkyl groups represented by the general following formula

(RS-c)

wherein

R 29 , R 30 , R 31 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , and where two or all of radicals R 29 , R 30 , R 31 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R 32 ;

R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

with the proviso that at each occurrence at least one of radicals R 29 , R 30 and R 31 is other than H and that at each occurrence at least one of radicals R 29 , R 30 and R 31 is or contains an aromatic ring system having at least 6 aromatic ring atoms;

or from aromatic ring systems represented by the general following formula (RS-d)

wherein

R 40 to R 44 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , and where two or more of radicals R 40 to R 44 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R 32 as defined above.

31 . Compound according to claim 25 , characterized in that R 2 and R A stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, N(Ar) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, P(═O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.

32 . Compound according to claim 25 , characterized in that R 2 and R A stand on each occurrence, identically or differently, for H, D, F, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, O or S and where one or more H atoms may be replaced by D, F, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.

33 . Compound according to claim 25 , characterized in that R 2 and R A stand on each occurrence, identically or differently,

for H, D, F, CN; or

for a group of formula (RS-a), a group of formula (RS-b), a group of formula (RS-c) or a group of formula (RS-d); or

for a group of formula (ArL-1),

where the dashed bond in formula (ArL-1) indicates the bonding to the structure of formula (1), where Ar 2 , Ar 3 stand on each occurrence, identically or differently, for an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R; and where m is an integer selected from 1 to 10;

RS-a is a branched or cyclic alkyl group represented by the general following formula (RS-a)

wherein

R 22 , R 23 , R 24 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 , and where two of radicals R 22 , R 23 , R 24 or all radicals R 22 , R 23 , R 24 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R 25 ;

R 25 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms;

with the proviso that at each occurrence at least one of radicals R 22 , R 23 and R 24 is other than H, with the proviso that at each occurrence all of radicals R 22 , R 23 and R 24 together have at least 4 carbon atoms and with the proviso that at each occurrence, if two of radicals R 22 , R 2 3, R 24 are H, the remaining radical is not a straight-chain;

RS-b is a branched or cyclic alkoxy group represented by the general following formula (RS-b)

wherein

R 26 , R 27 , R 28 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 as defined above, and where two of radicals R 26 , R 27 , R 28 or all radicals R 26 , R 27 , R 28 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R 25 as defined above;

with the proviso that at each occurrence only one of radicals R 26 , R 27 and R 28 may be H;

RS-c is an aralkyl group represented by the general following formula

(RS-c)

wherein

R 29 , R 30 , R 31 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , and where two or all of radicals R 29 , R 30 , R 31 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R 32 ;

R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

with the proviso that at each occurrence at least one of radicals R 29 , R 30 and R 31 is other than H and that at each occurrence at least one of radicals R 29 , R 30 and R 31 is or contains an aromatic ring system having at least 6 aromatic ring atoms;

RS-d is an aromatic ring system represented by the general following formula (RS-d)

wherein

R 40 to R 44 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , and where two or more of radicals R 40 to R 44 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R 32 as defined above.

34 . Compound according to claim 25 , characterized in that it is selected from compounds of formula (4),

where the symbols have the same meaning as in claim 25 .

35 . Compound according to claim 25 , characterized in that R B and R A are on each occurrence, identically or differently, selected

from branched or cyclic alkyl groups represented by the general following formula (RS-a)

wherein

R 22 , R 23 , R 24 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 , and where two of radicals R 22 , R 23 , R 24 or all radicals R 22 , R 23 , R 24 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R 25 ;

R 25 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms;

with the proviso that at each occurrence at least one of radicals R 22 , R 23 and R 24 is other than H, with the proviso that at each occurrence all of radicals R 22 , R 23 and R 24 together have at least 4 carbon atoms and with the proviso that at each occurrence, if two of radicals R 22 , R 2 3, R 24 are H, the remaining radical is not a straight-chain;

or from branched or cyclic alkoxy groups represented by the general following formula (RS-b)

wherein

R 26 , R 27 , R 28 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 as defined above, and where two of radicals R 26 , R 27 , R 28 or all radicals R 26 , R 27 , R 28 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R 25 as defined above;

with the proviso that at each occurrence only one of radicals R 26 , R 27 and R 28 may be H;

or from aralkyl groups represented by the general following formula

(RS-c)

wherein

R 29 , R 30 , R 31 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , and where two or all of radicals R 29 , R 30 , R 31 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R 32 ;

R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

with the proviso that at each occurrence at least one of radicals R 29 , R 30 and R 31 is other than H and that at each occurrence at least one of radicals R 29 , R 30 and R 31 is or contains an aromatic ring system having at least 6 aromatic ring atoms;

or from aromatic ring systems represented by the general following formula (RS-d)

wherein

R 40 to R 44 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , and where two or more of radicals R 40 to R 44 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R 32 as defined above.

36 . Compound according to claim 25 , characterized in that it is selected from compounds of formula (5) or (6),

wherein the group R A has the same meaning as in claim 25 , and

wherein, in formula (5),

R 40 , R 42 , R 44 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 ; where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

with the proviso that at least one of R 40 , R 42 , R 44 is other than H;

or

wherein, in formula (6),

R 41 , R 43 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 ; where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

with the proviso that at least one of R 41 , R 43 is other than H.

37 . Compound according to claim 36 , characterized in that

R 42 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 , where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

R 40 , R 44 are at each occurrence, identically or differently, selected from an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 ; where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms.

38 . Compound according to claim 25 , characterized in that it is selected from the compounds of formulae (5-1), (5-2) and (5-3),

where the group R A has the same meaning as in claim 25 , and where

in each of formulae (5-1), (5-2) and (5-3) the phenyl groups indicated with —R 32 are unsubstituted or substituted with one or more radicals R 32 ;

R 42 and R 44 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 ; where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms.

39 . Compound according to claim 25 , characterized in that it is selected from the compounds of formulae (5-1-a) to (5-3-g),

where the groups R A , R Y and R have the same meaning as in claim 25 , and

where in each of formulae (5-1-a) to (5-3-g), the phenyl groups indicated with —R 32 are unsubstituted or substituted with one or more radicals R 32 ;

R 42 and R 44 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 ; where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms.

40 . Compound according to claim 36 , characterized in that the groups R 40 , R 42 , R 44 are at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , where R 32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms.

41 . Polymer, oligomer or dendrimer containing one or more compounds according to claim 25 , where the bond(s) to the polymer, oligomer or dendrimer may be localised at any positions in formula (1) which is substituted by R 1 , R 2 , R A , R B or R.

42 . Formulation comprising at least one compound according to claim 25 and at least one solvent.

43 . Electronic device comprising at least one compound according to claim 25 , selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, dye-sensitised organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes and organic plasmon emitting devices.

44 . Organic electroluminescent device comprising at least one compound according to claim 25 , characterised in that the at least one compound is employed as an emitter in an emitting layer.

45 . Organic electroluminescent device according to claim 44 , characterized in that the at least one compound is employed as a fluorescent emitter in an emitting layer, wherein the emitting layer comprises at least one further component selected from matrix materials.

46 . Organic electroluminescent device according to claim 44 , characterized in that the at least one compound is employed as an emitter showing Thermally Activated Delayed Fluorescence in an emitting layer, wherein the emitting layer comprises at least one further component selected from matrix materials.

47 . Organic electroluminescent device according to claim 44 , characterized in that the at least one compound is employed as a fluorescent emitter in an emitting layer, wherein the emitting layer comprises at least one sensitizer selected from phosphorescent compounds and thermally activated delayed fluorescence compounds.

48 . Organic electroluminescent device according to claim 47 , characterized in that the emitting layer further comprises at least one organic functional material selected from matrix materials.

Assignments (4)
NUNC PRO TUNC ASSIGNMENT Recorded Feb 10, 2026
From: MERCK PATENT GMBH
To: UDC IRELAND LIMITED
Reel/Frame 073741/0249 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2022
From: STENGEL, ILONA; LACKNER, AARON; RODRIGUEZ, LARA-ISABEL; WALTER, CHARLOTTE; MEKIC, AMEL
To: MERCK KGAA
Reel/Frame 061046/0394 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2022
From: MERCK KGAA
To: MERCK PERFORMANCE MATERIALS GERMANY GMBH
Reel/Frame 061046/0472 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2022
From: MERCK PERFORMANCE MATERIALS GERMANY GMBH
To: MERCK PATENT GMBH
Reel/Frame 061046/0735 →