# US 2025/0098532 A1 · Nitrogenous compounds for organic electroluminescent devices

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- Number: US 2025/0098532 A1
- Document ID: US20250098532A1
- Status: Published application
- Kind: A1
- Application number: 18/273,794
- Filed: 2022-01-24
- Published: 2025-03-20
- Earliest claimed: 2021-01-25
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Amir Hossain PARHAM; Christian EHRENREICH
- Web page: https://patentgrep.com/patent/US20250098532A1

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 487/04: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to nitrogenous compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.

## Claims

### Claim at position 1

-19. (canceled)

### Claim 20

A compound comprising at least one structure of the formula (I):
where the symbols and indices used are as follows:
X is N or CR, with the proviso that not more than two of the X groups in one cycle are N;
T is an aromatic or heteroaromatic ring system which has 10 to 40 aromatic ring atoms and at least two fused aromatic heteroaromatic 6-membered rings and may be substituted by one or more R1 groups, where the ring substituted by the Ara and Arb groups are fused to an aryl or heteroaryl structure having at least two fused aromatic or heteroaromatic 6-membered rings;
W is the same or different at each instance and is O, S or NArb,
z is the same or different at each instance and is an integer in the range from 1 to 10;
Ara is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals;
Arb is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals;
R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R4)2, N(Ar′)2, CN, NO2, OR4, OAr′, SR4, SAr′, COOR4, C(═O)N(R4)2, Si(R4)3, B(OR4)2, C(═O)R4, P(═O)(R4)2, S(═O)R4, S(═O)2R4, OSO2R4, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R4)2, C═O, NR4, O, S or CONR4, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R4 radicals; at the same time, two R radicals together, or one R radical together with an R1, R2 radical, may also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R4)2, N(Ar′)2, CN, NO2, OR4, OAr′, SR4, SAr′, COOR4, C(═O)N(R4)2, Si(R4)3, B(OR4)2, C(═O)R4, P(═O)(R4)2, S(═O)R4, S(═O)2R4, OSO2R4, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R4)2, C═O, NR4, O, S or CONR4, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R4 radicals; at the same time, two R1 radicals together or one R1 radical together with one R, R2, R3 radical may also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
R2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R4)2, N(Ar′)2, CN, NO2, OR4, OAr′, SR4, SAr′, COOR4, C(═O)N(R4)2, Si(R4)3, B(OR4)2, C(═O)R4, P(═O)(R4)2, S(═O)R4, S(═O)2R4, OSO2R4, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R4)2, C═O, NR4, O, S or CONR4, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R4 radicals; at the same time, two R2 radicals together or one R2 radical together with one R, R1, R3 radical may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
R3 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R4)2, N(Ar′)2, CN, NO2, OR4, OAr′, SR4, SAr′, COOR4, C(═O)N(R4)2, Si(R4)3, B(OR4)2, C(═O)R4, P(═O)(R4)2, S(═O)R4, S(═O)2R4, OSO2R4, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R4)2, C═O, NR4, O, S or CONR4, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R4 radicals; at the same time, two R3 radicals together or one R3 radical together with one R1, R2 radical may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals;
R4 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R5)2, CN, NO2, OR5, SR5, Si(R5)3, B(OR5)2, C(═O)R5, P(═O)(R5)2, S(═O)R5, S(═O)2R5, OSO2R5, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R5 radicals and where one or more nonadjacent CH2 groups may be replaced by Si(R5)2, C═O, NR5, O, S or CONR5, 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 R2 radicals; at the same time, two or more R4 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
R5 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in which one or more hydrogen atoms may also be replaced by F.

### Claim 21 (depends on 20)

The compound as claimed in claim 20, wherein the T radical is selected from structures of the formulae (T-1) to (T-22)
where X′ is N or CR1, where R1 is as defined in claim 20;
there is at least one ring system of the formula (II) that binds to the T radical
where the symbols Ara and X have the definitions given in claim 20 and the dotted bonds represent the site of fusion to the T radical;
where there is at least one ring system of the formula (III) that binds to the T radical
where the symbols Arb and W have the definitions given in claim 20 and the dotted bonds represent the site of fusion to the T radical;
where one of the ring systems of the formulae (II), (III) is fused to the T radical at the positions identified by o, and one of the ring systems of the formulae (II), (III) is fused to the T radical at the positions identified by *.

### Claim 22 (depends on 20)

The compound as claimed in claim 20, wherein the T radical is selected from structures of the formulae (T′-1) to (T′-22)
where R1 has the definitions given in claim 20,
the index o is 0, 1 or 2;
the index m is 0, 1, 2, 3 or 4;
where there is at least one ring system of the formula (II) that binds to the T radical
where the symbols Ara and X have the definitions given in claim 20 and the dotted bonds represent the site of fusion to the T radical;
where there is at least one ring system of the formula (III) that binds to the T radical
where the symbols Arb and W have the definitions given in claim 20 and the dotted bonds represent the site of fusion to the T radical;
where one of the ring systems of the formulae (II), (III) is fused to the T radical at the positions identified by o, and one of the ring systems of the formulae (I), (II) is fused to the T radical at the positions identified by *.

### Claim 23 (depends on 20)

The compound as claimed in claim 20, comprising at least one structure of the formulae (I-1) to (I-118):
where X, X′, Ara and Arb have the definition given in claim 20.

### Claim 24 (depends on 20)

The compound as claimed in claim 20, comprising at least one structure of the formulae (I′-1) to (I′-118):
where R, R1, Ara and Arb have the definitions given in claim 20,
the index o is 0, 1 or 2,
the index m is 0, 1, 2, 3 or 4.

### Claim 25 (depends on 20)

The compound as claimed in claim 20, wherein two adjacent R1 groups do not form a fused aromatic heteroaromatic ring system with the groups to which the R1 groups bind, where this includes the R4 or R5 radicals, may be substituted by the R1 group.

### Claim 26 (depends on 20)

The compound as claimed in claim 20, wherein Ara and/or Arb are the same or different at each instance and are selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene and triphenylene, each of which may be substituted by one or more R2 or R3 radicals.

### Claim 27 (depends on 20)

The compound as claimed in claim 20, wherein R, R1, R2 and/or R3 are the same or different at each instance and are selected from the group consisting of H, D or an aromatic or heteroaromatic ring system selected from the groups of the following formulae Ar-1 to Ar-75, and/or the Ar group is the same or different at each instance and is selected from the groups of the following formulae Ar-1 to Ar-75:
where R4 has the definitions given above, the dotted bond represents the bond of the corresponding group and in addition:
Ar1 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R4 radicals;
A is the same or different at each instance and is C(R4)2, NR4, O or S;
p is 0 or 1, where p=0 means that the Ar1 group is absent and that the corresponding aromatic or heteroaromatic group is bonded directly to the corresponding radical;
q is 0 or 1, where q=0 means that no A group is bonded at this position and R4 radicals are bonded to the corresponding carbon atoms instead.

### Claim 28 (depends on 25)

The compound as claimed in claim 25, wherein the compounds have at least two electron-conducting groups.

### Claim 29 (depends on 20)

The compound as claimed in claim 20, wherein the Ara radical can be represented by a group of the formulae (Ar-47) to (Ar-51), (Ar-57), (Ar-58) and/or (Ar-63) to (Ar-68) shown above.

### Claim 30 (depends on 20)

A process for preparing The compound as claimed in claim 20, wherein an aromatic or heteroaromatic compound is reacted with an aromatic or heteroaromatic diamino compound by a coupling reaction.

### Claim 31 (depends on 20)

A composition comprising at least one matrix compound as claimed in claim 20 and at least one further matrix material, wherein the further matrix material is selected from compounds of one of the formulae (H-1), (H-2), (H-3), (H-4) and (H-5):
where the symbols and indices used are as follows:
R6 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R7)2, N(Ar″2, CN, NO2, OR7, SR7, COOR7, C(═O)N(R7)2, Si(R7)3, B(OR7)2, C(═O)R7, P(═O)(R7)2, S(═O)R7, S(═O)2R7, OSO2R7, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R7 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R7)2, C═O, NR7, O, S or CONR7, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R7 radicals; at the same time, two R6 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
Ar″ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R7 radicals;
A1 is C(R7)2, NR7, O or S;
Ar5 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R7 radicals;
R7 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R′)2, CN, NO2, OR′, SR′, Si(R′)3, B(OR′)2, C(═O)R′, P(═O)(R′)2, S(═O)R′, S(═O)2R8, OSO2R′, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R8 radicals and where one or more nonadjacent CH2 groups may be replaced by Si(R8)2, C═O, NR8, O, S or CONR8, 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 R8 radicals; at the same time, two or more R7 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
R8 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
v is the same or different at each instance and is 0, 1, 2, 3 or 4;
t is the same or different at each instance and is 0, 1, 2 or 3;
u is the same or different at each instance and is 0, 1 or 2.

### Claim 32 (depends on 20)

A composition comprising at least one matrix compound as claimed in claim 20 and at least one further matrix material, wherein the further matrix material is selected from compounds of one of the formulae (H-6), (H-7), (H-8), (H-9), (H-10), (H-11), (H-12) and (H-13):
where the symbols and indices used are as follows:
X2 is N or CR9, with the proviso that not more than two of the X2 groups in one cycle are N;
L2 is a connecting group which is selected from 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 R9 radicals;
Ar6 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R10 radicals;
R9 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R10)2, N(Ar′″)2, CN, NO2, OR10, SR10, COOR10, C(═O)N(R10)2, Si(R10)3, B(OR10)2, C(═O)R10, P(═O)(R10)2, S(═O)R10, S(═O)2R10, OSO2R10, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R10)2, C═O, NR10, O, S or CONR10, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R10 radicals; at the same time, two R9 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
Ar′″ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R10 radicals;
A2 is C(R10)2, NR10, O or S;
R10 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R11)2, CN, NO2, OR11, SR11, Si(R11)3, B(OR11)2, C(═O)R11, P(═O)(R11)2, S(═O)R11, S(═O)2R11, OSO2R11, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R11 radicals and where one or more nonadjacent CH2 groups may be replaced by Si(R11)2, C═O, NR11, O, S or CONR11, 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 R11 radicals; at the same time, two or more R10 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
R11 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
v is the same or different at each instance and is 0, 1, 2, 3 or 4;
t is the same or different at each instance and is 0, 1, 2 or 3;
x is the same or different at each instance and is 0, 1, 2, 3 or 4;
z is the same or different at each instance and is 0, 1 or 2, with the sum total of x and 2z is not more than 4.

### Claim 33 (depends on 31)

The composition as claimed in claim 31, wherein the compound has a proportion by mass in the composition in the range from 10% by weight to 95% by weight, based on the total mass of the composition.

### Claim 34 (depends on 20)

A formulation comprising at least one compound as claimed in claim 20 and at least one further compound, where the further compound is selected from one or more solvents.

### Claim 35 (depends on 30)

A formulation comprising at least one composition as claimed in claim 30 and at least one further compound, where the further compound is selected from one or more solvents.

### Claim 36 (depends on 20)

An electronic device comprising at least one compound as claimed in claim 20.

### Claim 37 (depends on 31)

An electronic device comprising the composition as claimed in claim 31.

### Claim 38 (depends on 20)

An organic electroluminescent device which comprises the compound as claimed in claim 20 is used as matrix material in an emitting layer and/or electron transport layer and/or in a hole blocker layer and/or in a hole transport layer and/or in an electron blocker layer.

### Claim 39 (depends on 31)

An electronic device which comprises the composition as claimed in claim 31, wherein in the compound is used as matrix material for phosphorescent emitters in combination with a further matrix material, where the further matrix material is selected from compounds of one of the formulae (H-1), (H-2), (H-3), (H-4) and (H-5):
where the symbols A1, Ar5 and R6 and the indices s, t and u have the definitions given in claim 31,
and/or the further matrix material is selected from compounds of one of the formulae (H-6), (H-7), (H-8), (H-9), (H-10), (H-11), (H-12) and (H-13):
wherein
X2 is N or CR9, with the proviso that not more than two of the X2 groups in one cycle are N;
L2 is a connecting group which is selected from 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 R9 radicals;
Ar6 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R10 radicals;
R9 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R10)2, N(Ar′″)2, CN, NO2, OR10, SR10, COOR10, C(═O)N(R10)2, Si(R10)3, B(OR10)2, C(═O)R10, P(═O)(R10)2, S(═O)R10, S(═O)2R10, OSO2R10, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R10)2, C═O, NR10, O, S or CONR10, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, and may be substituted in each case by one or more R10 radicals; at the same time, two R9 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
Ar′″ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R10 radicals;
A2 is C(R10)2, NR10, O or S;
R10 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R11)2, CN, NO2, OR11, SR11, Si(R11)3, B(OR11)2, C(═O)R11, P(═O)(R11)2, S(═O)R11, S(═O)2R11, OSO2R11, a straight-chain alkyl 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R11 radicals and where one or more nonadjacent CH2 groups may be replaced by Si(R11)2, C═O, NR11, O, S or CONR11, 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 R11 radicals; at the same time, two or more R10 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
R11 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
v is the same or different at each instance and is 0, 1, 2, 3 or 4;
t is the same or different at each instance and is 0, 1, 2 or 3;
x is the same or different at each instance and is 0, 1, 2, 3 or 4;
z is the same or different at each instance and is 0, 1 or 2, with the sum total of x and 2z is not more than 4.