IP Library Granted Patent US 11,581,495
Granted Patent B2
US 11,581,495 · App. 15/746,228 · Granted Feb 14, 2023

Phenyl derivatives substituted with at least two electron acceptors and at least two electron donors for use in organic electronic devices

Inventors: Amir Hossain Parham (Frankfurt Am Main, DE); Philipp Stoessel (Frankfurt Am Main, DE); Christof Pflumm (Darmstadt, DE); Anja Jatsch (Frankfurt Am Main, DE); Joachim Kaiser (Darmstadt, DE)
Assignee: MERCK PATENT GMBH
H01L51/0072C07D209/80C07D209/86C07D209/88C07D219/02C07D219/04C07D241/48C07D265/38C07D279/20C07D471/04C07F5/027C07F7/0816C08G61/124C08G73/0672H01L51/008H01L51/0035H01L51/0036H01L51/0039H01L51/0043H01L51/0071H01L51/0094C08G2261/11C08G2261/12C08G2261/132C08G2261/226C08G2261/228C08G2261/3142C08G2261/3241C08G2261/3245C08G2261/3246C08G2261/3247C08G2261/364C08G2261/41C08G2261/411C08G2261/412C08G2261/414C08G2261/514C08G2261/95H01L51/0002H01L51/5012H01L51/5072H01L51/5088H01L51/5096
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Quick Facts
Patent No.
US 11,581,495
App. No.
15/746,228
Granted
Feb 14, 2023
Kind
B2
Abstract

The present invention relates to a phenyl-derivative compound substituted with at least two electron acceptors and at least two electron donors. Formula (I) R A aR D bR S cC 6 wherein a is 2, 3 or 4; b is 2, 3 or 4; c is 0, 1 or 2; a+b−c=6; R A is at each occurrence independently a group with −M-effect; R B is at each occurrence independently a group with +−M-effect; R S is as defined in claim 1. Said compound is suited for use in organic electronic devices, particularly in organic electroluminescent devices.

Claims (26)

1. A compound of formula (I-B-22)

wherein

R A is at each occurrence independently a group with −M-effect and is selected from the group consisting of fluoroalkyl and aryl substituted with one or more electron withdrawing groups, wherein the electron withdrawing groups are selected from the group consisting of fluoroalkyl, F and CN;

R D is at each occurrence independently a group with +-M-effect;

R S is at each occurrence independently selected from the group consisting of linear alkyl group with 1 to 20 C-atoms or a branched or cyclic alkyl-, alkoxy- or thioalkyl-group with 3 to 20 C-atoms wherein these groups may be substituted with one or more of groups R 2 and wherein one or more H-atoms in these groups may be replaced by D, or an aromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 ; and

R 2 is at each occurrence independently selected from group consisting of H, D, aliphatic, aromatic and/or heteroaromatic hydrocarbyl group with 1 to 20 C-atoms, wherein two or more groups R 2 together may form a mono- or polycyclic aliphatic ring system.

2. The compound according to claim 1 , wherein R D is at each occurrence independently a group of general formula (II)

wherein

Ar 1 and Ar 2 are independently of each other selected from substituted or unsubstituted aryl or heteroaryl with 5 to 30 aromatic ring atoms;

Y is selected from the group consisting of a single bond, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , P(═S)R 1 , O, S, S═O and S(═O) 2 ; and

R 1 is at each occurrence independently selected from the group consisting of H, D, B(OR 21 ) 2 , CHO, C(═O)R 21 , CR 21 ═C(R 21 ), CN, C(═O)OR 21 , C(═O)N(R 21 ) 2 , Si(R 21 ) 3 , N(R 21 ) 2 , NO 2 , P(═O)(R 21 ) 2 , OSO 2 R 21 , OR 21 , S(═O)R 21 , S(═O) 2 R 21 , OH, SH, linear alkyl-, alkoxy- or thioalkyl-group with 1 to 20 C-atoms or a branched or cyclic alkyl-, alkoxy- or thioalkyl-group with 3 to 20 C-atoms or an alkenyl- or alkinyl-group with 2 to 20 C-atoms, wherein these groups may be substituted with one or more of groups R 2 and wherein one or more CH 2 -groups in these groups may be replaced by —R 21 C═CR 21 —, —C≡C—, Si(R 21 ) 2 , C═O, C═S, C═NR 21 , —C(═O)O—, —C(═O)NR 21 —, NR 21 , P(═O)(R 21 ) , —O—, —S—, SO or SO 2 , and wherein one or more H-atoms in these groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 21 or an aryloxy- or heteroaryloxy-group with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 21 , or an aralkyl- or heteroaralkyl-group with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 21 , wherein two or more groups R 21 may be linked with each other and form an aliphatic or aromatic or heteroaromatic ring;

R 21 is at each occurrence independently selected from group consisting of H, D, F, aliphatic, aromatic and/or heteroaromatic hydrocarbyl group with 1 to 20 C-atoms, in which one or more hydrogen atoms may be replaced by F, wherein two or more groups R 2 together may form a mono- or polycyclic aliphatic ring system.

3. An oligomer, polymer or dendrimer comprising one or more of the compounds of claim 1 , wherein at least one bond to the oligomer, polymer or dendrimer is on any one or more of groups R A , R D or R S .

4. A formulation comprising a solvent and the compound of claim 1 .

5. A formulation comprising a solvent and the oligomer, polymer or dendrimer of claim 3 .

6. An electronic device selected from the group consisting of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organischen photovoltaic cells, organic optical detectors, organic photoreceptors, organic field-quench-devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-Laser) and organic electroluminescence devices (OLEDs), wherein the electronic devices comprises the compound of claim 1 .

7. An organic electroluminescent device which comprises an anode, a cathode and at least one organic layer, said organic layer comprising the compound of claim 1 as matrix material in an emitting layer in combination with one or more dopants, or that it is comprised as electron transport material in an electron transport layer, an electron injection layer or a hole blocking layer.

8. An electronic device which comprises the compound as claimed in claim 1 .

9. A method of producing the electronic device of claim 8 , said method comprising the steps of

(a) providing a compound of claim 1 or the oligomer, polymer or dendrimer of claim 3 ; and

(b) depositing said compound or said oligomer, polymer or dendrimer on a supporting layer.

10. The compound according to claim 1 , wherein

R A is at each occurrence independently a group with −M-effect selected from fluoroalkyl.

11. The compound according to claim 1 , wherein

R A is at each occurrence independently a group with −M-effect and is selected from the group consisting of fluoroalkyl and aryl substituted with one or more electron withdrawing groups, wherein the electron withdrawing groups are selected from the group consisting of fluoroalkyl and F.

12. The compound according to claim 1 , wherein R S is at each occurrence independently selected from the group consisting of a linear alkyl group with 1 to 20 C-atoms or a branched or cyclic alkyl-, alkoxy- or thioalkyl-group with 3 to 20 C-atoms wherein these groups may be substituted with one or more of groups R 2 and wherein one or more H-atoms in these groups may be replaced by an aromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 .

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Feb 10, 2026
From: MERCK PATENT GMBH
To: UDC IRELAND LIMITED
Reel/Frame 073741/0073 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2018
From: PARHAM, AMIR HOSSAIN; STOESSEL, PHILIPP; KAISER, JOACHIM; JATSCH, ANJA; PFLUMM, CHRISTOF
To: MERCK PATENT GMBH
Reel/Frame 044938/0725 →
Priority Claims (1)
GB 1513037 · Jul 23, 2015 · national
Continuity (1)
Related Publication 20180226586A1 · Aug 9, 2018