# US 2018/0026202 A1 · Organic molecules for use in optoelectronic devices

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- Number: US 2018/0026202 A1
- Document ID: US20180026202A1
- Status: Published application
- Kind: A1
- Application number: 15/541,590
- Filed: 2016-07-04
- Published: 2018-01-25
- Earliest claimed: 2015-07-03
- Assignees: Cynora GmbH
- Applicants: Cynora GmbH
- Inventors: Michael Danz; Daniel Zink
- Web page: https://patentgrep.com/patent/US20180026202A1

## CPC

- C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C07D 209/56: Ring systems containing three or more rings
- C07D 209/80: [b, c]- or [b, d]-condensed
- C07D 209/82: Carbazoles; Hydrogenated carbazoles
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D 215/06: having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
- C07D 219/08: Nitrogen atoms
- C07D 219/14: with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D 241/48: with hydrocarbon radicals, substituted by nitrogen atoms, directly attached to the ring nitrogen atoms
- C07D 265/38: [b, e]-condensed with two six-membered rings
- C07D 279/02: 1,2-Thiazines; Hydrogenated 1,2-thiazines
- C07D 279/22: with carbon atoms directly attached to the ring nitrogen atom
- C07D 279/26: without other substituents attached to the ring system
- C07D 279/34: with hetero atoms directly attached to the ring sulfur atom
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/10: linked by a carbon chain containing aromatic rings
- C07D 409/14: containing three or more hetero rings
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D 417/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- C07F 7/0816: {said ring comprising Si as a ring atom}
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 57/008: {Triarylamine dyes containing no other chromophores}
- C09K 11/06: containing organic luminescent materials
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/12: comprising dopants
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/18: Carrier blocking layers
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 71/164: {using vacuum deposition}
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The invention relates to an organic molecule having precisely two units of formula I linked to one another via a single bond or a bridge Y where Y=a divalent group; X=at each occurrence identically or differently CN and CF3; D=chemical unit having a structure of the formula I-1: where #=attachment point of the unit of formula I-1 to the structure of formula I; A and B=independently of one another selected from the group consisting of CRR1, CR, NR, N, there being a single or double bond between A and B and a single or double bond between B and Z; Z=a direct bond or a divalent organic bridge which is a substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group or a combination thereof, —CRR1, —C═CRR1, —C═NR, —NR—, —O—, —SiRR1—, —S—, —S(O)—, —S(O)2—, O-interrupted substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group, phenyl units or substituted phenyl units.

## Claims

### Claim at position 1

1-19. (canceled)

### Claim 20

An organic molecule having two units of formula I linked to one another via a single bond or a bridge Y,
where
Y=a divalent chemical group;
X=at each occurrence independently of one another is selected from the group consisting of CN and CF3;
D=a chemical unit having a structure of the formula I-1:
wherein
#=is an attachment point of the unit of formula I-1 to the structure of formula I;
A and B=independently of one another are selected from the group consisting of CRR1, CR, NR, and N, with there being a single or double bond between A and B and a single or double bond between B and Z;
Z=a direct bond or a divalent organic bridge which is a substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group or a combination thereof, —CRR1, —C═CRR1, —C═NR, —NR—, —O—, —SiRR1—, —S—, —S(O)—, —S(O)2—, O-interrupted substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group, phenyl units or substituted phenyl units;
where each R and R1 are identical or different at each occurrence and are H, deuterium, azide (N3−), F, Cl, Br, I, N(R2)2, CN, CF3, NO2, OH, COOH, COOR2, CO(NR2)2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a linear alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which in each case may be substituted by one or more radicals R2, it being possible for one or more non-adjacent CH2 groups to be 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 it being possible for one or more H atoms to be replaced by deuterium, F, Cl, Br, I, CN, CF3 or NO2, or is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R2, or is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, wherein this ring system is optionally substituted by one or more radicals R2, or is a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms wherein this ring system is optionally substituted by one or more radicals R2, or is a combination of these systems, or is a crosslinkable unit QE which may be crosslinked by acid-catalytic, thermal or UV crosslinking methods in the presence or absence of a photoinitiator or by microwave radiation; optionally two or more of these substituents R and R1 may form with one another a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system;
R2, identically or differently at each occurrence, is H, deuterium, F, Cl, Br, I, N(R3)2, CN, CF3, NO2, OH, COOH, COOR3, CO(NR3)2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a linear alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may be substituted in each case by one or more radicals R3, it being possible for one or more non-adjacent CH2 groups to be replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3, and it being possible for one or more H atoms to be replaced by deuterium, F, Cl, Br, I, CN, CF3 or NO2, or is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R3, or is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted by one or more radicals R3, or is a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms wherein this ring system is optionally substituted by one or more radicals R3, or is a combination of these systems; where optionally two or more of these substituents R2 form with one another a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system;
R3, identically or differently at each occurrence, is H, deuterium, F, CF3 or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF3; where optionally two or more substituents R3 form with one another a mono- or polycyclic, aliphatic ring system;
R′=attachment position for the second unit of the formula I or selected from the group consisting of Y, H, N(R4)2, OR4, a linear alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms wherein this system is optionally substituted in each case by one or more radicals R4, and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R4;
R″=attachment position for the second unit of the formula I or selected from the group consisting of Y, N(R4)2, OR4, a linear alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms wherein this group is optionally substituted in each case by one or more radicals R4, and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R4;
with the proviso that if R′ is Y, R″ is not Y, and, if R″ is Y, R′ is not Y;
and with the proviso that if R′ is the attachment position for the second unit of the formula I, R″ is not the attachment position for the second unit of the formula I, and, if R″ is the attachment position for the second unit of the formula I, R′ is not the attachment position for the second unit of the formula I;
R4, identically or differently at each occurrence, is H, deuterium, N(R5)2, Si(R5)3, a linear 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 wherein this group is optionally substituted in each case by one or more radicals R5, or is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R5, or is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms wherein this group is optionally substituted by one or more radicals R5, or is a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms wherein this ring system is optionally substituted by one or more radicals R5, or is a combination of these systems; where optionally two or more of these substituents R5 may also form with one another a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system; and
R5, identically or differently at each occurrence, is H, deuterium or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms; where optionally two or more substituents R5 form with one another a mono- or polycyclic, aliphatic ring system.

### Claim 21 (depends on 20)

The organic molecule according to claim 20, wherein
R′=the attachment position for the second unit of the formula I or selected from the group consisting of Y, H, N(R4)2, OR4, a linear alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms wherein this group is optionally substituted in each case by one or more radicals R4, and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R4; and
R″=the attachment position for the second unit of the formula I or selected from the group consisting of Y, N(R4)2, OR4, a linear alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms wherein this group is optionally to be substituted in each case by one or more radicals R4, and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted in each case by one or more radicals R4;
wherein the heteroaromatic ring system is not an N-heteroaromatic;
wherein, if R′ is Y, R″ is not Y, and, if R″ is Y, R′ is not Y;
wherein if R′ is the attachment position for the second unit of the formula I, then R″ is not the attachment position for the second unit of the formula I, and, if R″ is the attachment position for the second unit of the formula I, then R′ is not the attachment position for the second unit of the formula I; and
wherein Y and R4 have the aforestated meanings.

### Claim 22 (depends on 20)

The organic molecule according to claim 20, wherein
R′=the attachment position for the second unit of the formula I or selected from the group consisting of Y, H, N(R4)2, OR4, thiophene which may be substituted by one or more radicals R4, a linear alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms wherein this group is optionally substituted in each case by one or more radicals R4, and an aromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted by one or more radicals R4;
R″=the attachment position for the second unit of the formula I or selected from the group consisting of Y, N(R4)2, OR4, thiophene which may be substituted by one or more radicals R4, a linear alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms wherein this group is optionally substituted in each case by one or more radicals R4, and an aromatic ring system having 5 to 60 aromatic ring atoms wherein this ring system is optionally substituted by one or more radicals R4;
wherein if R′ is Y, then R″ is not Y, and, if R″ is Y, then R′ is not Y;
and wherein if R′ is the attachment position for the second unit of the formula I, then R″ is not the attachment position for the second unit of the formula I, and, if R″ is the attachment position for the second unit of the formula I, then R′ is not the attachment position for the second unit of the formula I;
wherein Y and R4 have the aforestated meanings.

### Claim 23 (depends on 20)

The organic molecule according to claim 20, wherein
R′ is H and R″ is the attachment point for the second unit of the formula I or is Y; wherein Y has the aforestated meaning.

### Claim 24 (depends on 20)

The organic molecule according to claim 20, wherein the donor group having electron-donating properties of the formula I-1 has a structure of the formula II:
where #, Z and R have the aforestated meanings.

### Claim 25 (depends on 20)

The organic molecule according to claim 20, wherein the donor group having electronic-donating properties of the formula I-1 has a structure of the formula III:
where # and R have the aforestated meanings.

### Claim 26 (depends on 20)

The organic molecule according to claim 20, wherein the organic molecule has a structure of the formula XII:
where n=0 or 1;
and where D, R′ and X have the aforestated meanings.

### Claim 27 (depends on 26)

The organic molecule according to claim 26, wherein R′ is H.

### Claim 28 (depends on 20)

The organic molecule according to claim 20, wherein the accepting unit X of the formula I is CN.

### Claim 29 (depends on 20)

The organic molecule according to claim 20, wherein the accepting unit X of the formula I is CF3.

### Claim 30 (depends on 20)

The organic molecule according to claim 20, wherein the bridge Y is selected from the structures of the formulae IV to X
wherein
#=the attachment point of the bridge Y to the structure of formula I.

### Claim 31 (depends on 28)

The organic molecule according to claim 28, wherein the bridge Y is selected from the structures of the formulae IV to X
wherein
#=the attachment point of the bridge Y to the structure of formula I.

### Claim 32 (depends on 29)

The organic molecule according to claim 29, wherein the bridge Y is selected from the structures of the formulae IV to X
wherein
#=the attachment point of the bridge Y to the structure of formula I.

### Claim 33 (depends on 20)

A process for preparing an organic molecule according to claim 20, comprising coupling one unit of formula I to another unit of formula I.

### Claim 34 (depends on 20)

An optoelectronic device comprising an organic molecule according to claim 20.

### Claim 35 (depends on 34)

The optoelectronic device according to claim 34, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

### Claim 36 (depends on 34)

The optoelectronic device according to claim 34, wherein the organic molecule is one of an emitter and an absorber in the optoelectronic component.

### Claim 37 (depends on 34)

The optoelectronic device according to claim 34, wherein the proportion of the organic molecule in the emitter or absorber is in the range of 1% to 99%.

### Claim 38 (depends on 20, 35)

The optoelectronic device according to claim 35, comprising
a substrate,
an anode and
a cathode, wherein the anode or the cathode is applied to the substrate, and at least one light-emitting layer is disposed between anode and cathode and which comprises the organic molecule according to claim 20.

### Claim 39 (depends on 20)

A process for producing an optoelectronic component, comprising processing of the organic molecule according to claim 20 by a vacuum vaporization process or from a solution.