[특허]Organic electronic component, use of a zinc complex as a p-dopant for organic electronic matrix materials

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Organic electronic component, use of a zinc complex as a p-dopant for organic electronic matrix materials

특허상세정보
국가/구분	United States(US) Patent 등록
국제특허분류(IPC7판)	H01L-051/50 H01L-051/00
출원번호	US-0515858 (2015-09-28)
등록번호	US-10256422 (2019-04-09)
우선권정보	DE-10 2014 114 224 (2014-09-30)
국제출원번호	PCT/EP2015/072283 (2015-09-28)
국제공개번호	WO2016/050705 (2016-04-07)
발명자 / 주소	Schmid, Guenter Maltenberger, Anna Pecqueur, Sebastien Kessler, Florian Regensburger, Stefan
출원인 / 주소	OSRAM OLED GMBH
대리인 / 주소	Slater Matsil, LLP
인용정보	피인용 횟수 : 0 인용 특허 : 13

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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 R1 and R2 can be oxygen, sulphur, selenium, NH or NR4 independently selected from one another, wherein R3 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 R4 is selected from the group consisting of alkyl and aryl which can be bonded to R3.

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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 R1 and R2 are independently from one another selected from the group consisting of oxygen, sulfur, selenium, NH and NR4,wherein R3 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 CH2 groups are replaceable by —O—, —S—, —NH—, —NRooo—, —SiRoRoo—, —CO—, —COO—, —CORoORoo—, —OCO—, —OCO—O—, —SO2—, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1═CY2 or —C≡C—independently from one another in such a way that O and/or S atoms are not directly bonded to one another, andO and/or S atoms are replaceable with aryl or heteroaryl containing 1 to 30 C atoms,wherein R4 is selected from the group consisting of alkyl and aryl and is bondable to R3,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 R3 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 R3 is selected from the group consisting of: wherein Y1—Y5 are selected independently of one another from the group consisting of C—H, C-D, C—F, C—NO2, C—CN, C-halogen, C-pseudohalogen, N and C—CnF2n+1 with n=1 to 10. 4. The component according to claim 1, wherein R3 is selected from the group consisting of: wherein Y1—Y7 are selected independently of one another from the group consisting of C—H, C-D, C—F, C—NO2, C—CN, C-halogen, C-pseudohalogen, N and C—CNF2N +1 with n=1 to 10. 5. The component according to claim 1, wherein R3 is selected from the group consisting of: wherein Y1—Y7 are selected independently of one another from the group consisting of C—H, C-D, C—F, C—No2, C—CN, C-halogen, C-pseudohalogen and C—CNF2N+1 with n =1 to 10. 6. The component according to claim 1, wherein both R1 and R2 are oxygen. 7. The component according to claim 1, wherein the zinc complex further comprises at least one further ligand LC, which is bonded to zinc via a carbon atom. 8. The component according to claim 7, wherein the at least one ligand LC 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 R1 and R2 are selected independently from one another from the group consisting of oxygen, sulfur, selenium, NH and NR4,wherein R3 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 CH2groups are replaceable by —O—, —S—, —NH—, —NRooo—, —SiRoRoo—, —CO—, —COO—, —CORo ORoo—, —OCO——OCO—O—, —SO2—, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1═CY2 or —C≡C—independently from one another in such a way that O and/or S atoms are not directly bonded to one another, andO and/or S atoms are replaceable with aryl or heteroaryl containing 1 to 30 C atoms,wherein R4 is selected from the group consisting of alkyl and aryl and are bondable to R3,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 R1 and R2 are selected independently from one another from the group consisting of oxygen, sulfur, selenium, NH and NR4 ,wherein R3 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 CH2 groups are replaceable by —O—, —S—, —NH—, —NRooo—, —SiRoRoo—, —CO—, —COO—, —CORoORoo—, —OCO—, —OCO—O—, —SO2—, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1═CY2 or —C≡C—independently from one another in such a way that O and/or S atoms are not directly bonded to one another, andO and/or S atoms are replaceable with aryl or heteroaryl containing 1 to 30 C atoms,wherein R4 is selected from the group consisting of alkyl and aryl and is bondable to R3, andwherein the mononuclear zinc complex comprises the following structural unit: or the polynuclear zinc complex comprises one of the following structural units:

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Organic electronic component, use of a zinc complex as a p-dopant for organic electronic matrix materials

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Organic electronic component, use of a zinc complex as a p-dopant for organic electronic matrix materials

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