Organic electronic component, use of a zinc complex as a p-dopant for organic electronic matrix materials
An organic electronic component and a method for making an organic electronic component with a p-dopant are disclosed. In an embodiment, the component includes a matrix containing a zinc complex as a p-dopant, the zinc complex containing at least one ligand L of the following structure: formula (I) wherein R 1 and R 2 can be oxygen, sulphur, selenium, NH or NR 4 independently selected from one another, wherein R 3 may comprise alkyl, long-chain alkyl, cycloalkyl, halogen-alkyl, aryl, arylene, halogen-aryl, heteroaryl, heteroarylene, heterocyclic-alkylene, heterocycloalkyl, halogen-heteroaryl, alkenyl, halogen-alkenyl, alkynyl, halogen-alkynyl, ketoaryl, halogen-ketoaryl, ketoheteroaryl, ketoalkyl, halogen-ketoalkyl, ketoalkenyl, halogen-ketoalkenyl, halogen-alkyl-aryl or halogen-alkyl-heteroaryl, and wherein R 4 is selected from the group consisting of alkyl and aryl which can be bonded to R 3 .
1. An organic electronic component comprising:
a matrix comprising a zinc complex as a p-dopant, the zinc complex containing a zinc atom in the oxidation state II and at least one ligand L of the following structure:
wherein R 1 and R 2 are independently from one another selected from the group consisting of oxygen, sulfur, selenium, NH and NR 4 ,
wherein R 3 is selected from the group consisting of alkyl, long-chain alkyl, cycloalkyl, haloalkyl, aryl, arylene, haloaryl, heteroaryl, heteroarylene, heterocycloalkylene, heterocycloalkyl, haloheteroaryl, alkenyl, haloalkenyl, alkinyl, haloalkinyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, haloalkylaryl and haloalkylheteroaryl,
wherein one or more non-adjacent CH 2 groups are replaceable by —O—, —S—, —NH—, —NR ooo —, —SiR o R oo —, —CO—, —COO—, —COR o OR oo —, —OCO—, —OCO—O—, —SO 2 —, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY 1 ═CY 2 or —C≡C—independently from one another in such a way that O and/or S atoms are not directly bonded to one another, and
O and/or S atoms are replaceable with aryl or heteroaryl containing 1 to 30 C atoms,
wherein R 4 is selected from the group consisting of alkyl and aryl and is bondable to R 3 ,
wherein the zinc complex comprises at least one of the following structural units:
wherein M is a metal atom different from zinc.
2. The component according to claim 1 , wherein R 3 is selected from the group consisting of haloalkyl, haloaryl, haloheteroaryl, haloalkylaryl and haloalkylheteroaryl, and wherein the halogen is fluorine.
3. The component according to claim 1 , wherein R 3 is selected from the group consisting of:
wherein Y 1 —Y 5 are selected independently of one another from the group consisting of C—H, C-D, C—F, C—NO 2 , C—CN, C-halogen, C-pseudohalogen, N and C—C n F 2n+1 with n=1 to 10.
4. The component according to claim 1 , wherein R 3 is selected from the group consisting of:
wherein Y 1 —Y 7 are selected independently of one another from the group consisting of C—H, C-D, C—F, C—NO 2 , C—CN, C-halogen, C-pseudohalogen, N and C—C N F 2N + 1 with n=1 to 10.
5. The component according to claim 1 , wherein R 3 is selected from the group consisting of:
wherein Y 1 —Y 7 are selected independently of one another from the group consisting of C—H, C-D, C—F, C—No 2 , C—CN, C-halogen, C-pseudohalogen and C—C N F 2N+1 with n =1 to 10.
6. The component according to claim 1 , wherein both R 1 and R 2 are oxygen.
7. The component according to claim 1 , wherein the zinc complex further comprises at least one further ligand L C , which is bonded to zinc via a carbon atom.
8. The component according to claim 7 , wherein the at least one ligand L C is a substituted, unsubstituted, branched, linear or cyclic alkyl, or a substituted, unsubstituted aryl or heteroaryl.
9. The component according to claim 1 , wherein zinc has the coordination number 4, 5 or 6.
10. The component according to claim 1 , wherein the zinc complex is a trinuclear or pentanuclear metal complex.
11. The component according to claim 1 , wherein the zinc complex is a polynuclear metal complex, and wherein the at least one ligand L coordinately bonds two metal atoms.
12. The component according to claim 1 , wherein the zinc complex is a polynuclear metal complex comprising at least two ligands L, wherein at least one of the ligands L coordinately bonds two metal atoms, and wherein at least one further ligand L is bonded terminally to a metal center of the zinc complex.
13. The component according to claim 1 , wherein the zinc complex comprises at least two zinc atoms.
14. The component according to claim 1 , wherein the zinc complex further comprises a metal different from zinc.
15. A method for making an electronic component, the method comprising:
doping a matrix material of the electronic component with a p-dopant, wherein the p-dopant comprises a zinc complex comprising a zinc atom in the oxidation state II and at least one ligand L of the following structure:
wherein R 1 and R 2 are selected independently from one another from the group consisting of oxygen, sulfur, selenium, NH and NR 4 ,
wherein R 3 is selected from the group consisting of alkyl, long-chain alkyl, cycloalkyl, haloalkyl, aryl, arylene, haloaryl, heteroaryl, heteroarylene, heterocycloalkylene, heterocycloalkyl, haloheteroaryl, alkenyl, haloalkenyl, alkinyl, haloalkinyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, haloalkylaryl and haloalkylheteroaryl,
wherein one or more non-adjacent CH 2 groups are replaceable by —O—, —S—, —NH—, —NR ooo —, —SiR o R oo —, —CO—, —COO—, —COR o OR oo —, —OCO——OCO—O—, —SO 2 —, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY 1 ═CY 2 or —C≡C—independently from one another in such a way that O and/or S atoms are not directly bonded to one another, and
O and/or S atoms are replaceable with aryl or heteroaryl containing 1 to 30 C atoms,
wherein R 4 is selected from the group consisting of alkyl and aryl and are bondable to R 3 ,
wherein the zinc complex comprises at least one of the following structural units:
wherein M is a metal atom different from zinc.
16. The method according to claim 15 , wherein the zinc complex is a mononuclear or a polynuclear complex and comprises a zinc atom in the oxidation stage II, and wherein the mononuclear zinc complex comprises the following structural unit:
or the polynuclear zinc complex comprises one of the following structural units:
17. An organic electronic component comprising:
a matrix comprising a mononuclear or a polynuclear zinc complex as a p-dopant, the zinc complex comprises a zinc atom in the oxidation state II and contains at least one ligand L of the following structure:
wherein R 1 and R 2 are selected independently from one another from the group consisting of oxygen, sulfur, selenium, NH and NR 4 ,
wherein R 3 is selected from the group consisting of alkyl, long-chain alkyl, cycloalkyl, haloalkyl, aryl, arylene, haloaryl, heteroaryl, heteroarylene, heterocycloalkylene, heterocycloalkyl, haloheteroaryl, alkenyl, haloalkenyl, alkinyl, haloalkinyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, haloalkylaryl and haloalkylheteroaryl,
wherein one or more non-adjacent CH 2 groups are replaceable by —O—, —S—, —NH—, —NR ooo —, —SiR o R oo —, —CO—, —COO—, —COR o OR oo —, —OCO—, —OCO—O—, —SO 2 —, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY 1 ═CY 2 or —C≡C—independently from one another in such a way that O and/or S atoms are not directly bonded to one another, and
O and/or S atoms are replaceable with aryl or heteroaryl containing 1 to 30 C atoms,
wherein R 4 is selected from the group consisting of alkyl and aryl and is bondable to R 3 , and
wherein the mononuclear zinc complex comprises the following structural unit:
or the polynuclear zinc complex comprises one of the following structural units: