# US 8,785,636 B2 · Substituted indoloacridines for organic electroluminescent devices

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- Number: US 8,785,636 B2
- Document ID: US8785636B2
- Status: Granted
- Kind: B2
- Application number: 13/500,377
- Filed: 2010-09-09
- Published: 2012-08-09
- Granted: 2014-07-22
- Earliest claimed: 2009-10-08
- Assignees: Merck Patent GmbH
- Applicants: Amir Hossain Parham; Christof Pflumm
- Inventors: Amir Hossain Parham; Christof Pflumm
- Web page: https://patentgrep.com/patent/US8785636B2

## CPC

- C07D 471/04: Ortho-condensed systems
- C07D 471/16: Peri-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 487/16: Peri-condensed systems
- C09B 57/00: Other synthetic dyes of known constitution
- C09K 11/06: containing organic luminescent materials
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to compounds of the formula (1) and formula (2) which are suitable for use in electronic devices, in particular organic electroluminescent devices.

## Claims

### Claim 1

A compound of the formula (1) or formula (2):
where the following applies to the symbols and indices used:
X is, on each occurrence, N;
Y is, on each occurrence, identically or differently, C(R)2, C═O, C═S, C═NR or C═C(R)2;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R1)2, C(═O)Ar, C(═O)R1, P(═O)(Ar)2, 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by R1C═CR1, C≡C, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R1, or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R1;
R1 is on each occurrence, identically or differently, a H, D, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R2)2, C(═O)Ar, C(═O)R2, P(═O)(Ar)2, 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R2;
R2 is a H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R2 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R2; two radicals Ar which are bonded to the same N atom or P atom here may also be bridged to one another by a single bond or a bridge selected from N(R2), C(R2)2 or O;
L is a divalent or polyvalent straight-chain alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 1 to 40 C atoms or a branched or cyclic alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 3 to 40 C atoms or an alkenylene or alkynylene group having 2 to 40 C atoms, which is optionally substituted by in each case one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by —R1C═CR1—, —C≡C—, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)R1, S═O, SO2, —O—, —S— or —CONR1— and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an at least divalent aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which is optionally substituted by one or more radicals R1, or P(R1)3-p, P(═O)(R1)3-p, C(R1)4-p, Si(R1)4-p, N(Ar)3-p or a combination of two, three, four or five of these systems; or L is a chemical bond;
p is 2, 3, 4, 5 or 6, with the proviso that p is not greater than the maximum valence of L;
wherein at least one radical R stands for one of the groups of the following formula (3), formula (4), formula (5), or formula (6):
and/or wherein at least one group L stands for a group of the following formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15):
where the symbols used have the meanings given above, and the index m stands for 0 or 1; and * indicates the position of the bonding of the group of the formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15).

### Claim 2 (depends on 1)

The compound according to claim 1 of the formula (25), formula (26), formula (27), formula (32), formula (33), formula (34), formula (35), formula (36), formula (37) formula (44), formula (45), or formula (48):
where R represents a group of one of the formula (3), formula (4), formula (5), or formula (6), and where L in formula (48) represents a group of one of the formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15), Y stands, identically or differently, on each occurrence, for C(R)2, where R which is bonded in the C(R)2 group stands, identically or differently on each occurrence, for an alkyl group having 1 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms; furthermore, the C atoms drawn as unsubstituted may also be substituted by D instead of H.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein R represents a group of one of the formula (3), formula (4), formula (5), or formula (6), and where L in formula 48 represents a group of one of the formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15), Y stands, identically on each occurrence, for C(R)2, where R which is bonded in the C(R)2 group stands, identically or differently on each occurrence, for an alkyl group having 1 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, and at least one of the radicals R in these groups represents an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which optionally in each case be substituted by one or more radicals R1; furthermore, the C atoms drawn as unsubstituted may also be substituted by D instead of H.

### Claim 4 (depends on 2)

The compound according to claim 2, wherein the structures of the formula (25), formula (26), formula (27), formula (32), formula (33), formula (34), formula (35), formula (36), formula (37), formula (44), formula (45), formula (48), each contain a radical R in the position para to the central atom N, where the substituents R in the position para to the central atom N which do not stand for a group of the formula (3), formula (4), formula (5), or formula (6) stand for an alkyl group having 1 to 10 C atoms, or for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R1.

### Claim 5 (depends on 2)

The compound according to claim 2, wherein the structures of the formula (25), formula (26), formula (27), formula (32), formula (33), formula (34), formula (35), formula (36), formula (37), formula (44), formula (45), formula (48), each contain a radical R in the position para to the central atom N, where the substituents R in the position para to the central atom N which do not stand for a group of the formula (3), formula (4), formula (5), or formula (6) stand for an alkyl group having 1 to 4 C atoms, or for a phenyl group, which is optionally substituted by one or more radicals R1.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein Y is C(R)2.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein L is a divalent or polyvalent straight-chain alkylene group having 1 to 10 C atoms or a branched or cyclic alkylene group having 3 to 10 C atoms, which is optionally substituted by in each case one or more radicals R1, where one or more H atoms is optionally replaced by D or F, or an at least divalent aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R1; or L is a chemical bond; or L is a group of one of the formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15).

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R is selected, identically or differently on each occurrence, from the group consisting of H, D, F, Cl, Br, CN, N(Ar)2, C(═O)Ar, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms or an alkenyl or alkynyl group having 2 to 10 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by O and where one or more H atoms is optionally replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R1, or a combination of these systems, where at least one radical R represents a group of the formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), or formula (9).

### Claim 9 (depends on 1)

The compound according to claim 1, wherein the groups R which are bonded in Y are selected, identically or differently on each occurrence, from aromatic or heteroaromatic ring systems having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or in that one radical R, if Y stands for C(R)2, represents an alkyl group having 1 to 10 C atoms and the other radical R bonded to this carbon atom represents an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which is optionally substituted by one or more radicals R1.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein, in the structures of the formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15), the symbol R1 stands for an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which contains no condensed aromatic ring systems having more than 10 aromatic ring atoms and which may in each case be substituted by one or more radicals R2.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein, in the structures of the formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15), the symbol R1 stands for phenyl, ortho-, meta- or para-biphenyl, ortho-, meta- or para-terphenyl, quaterphenyl or 1- or 2-naphthyl, each of which is optionally substituted by one or more radicals R2.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein the group Ar in the formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), or formula (15), stands for an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which contains no condensed aromatic ring systems having more than 10 aromatic ring atoms and which is optionally substituted by one or more non-aromatic radicals R1.