Let $f : B_1(0)\setminus \{0\} \rightarrow \mathbb{C}$ be holomorphic with a pole in $0$ and assume that $f$ is injective on $B_1(0)\setminus \{0\}\cap \{z : \text{Re} z > 0\}$.
What can the order of the pole at $0$ be?
My Idea: Let $n$ be the order of the pole. Consider $g(z)=1/f(z)$. Then $g$ is also injective on the right half plane and $n$ is the order of the zero of $g$ at $0$. Now expand $g$ into a power series around $0$, $g(z) = az^n + h(z)$ with $h \in O(z^{n+1})$. Wlog $a=1$, because otherwise we can compose $g$ with a $z\mapsto \frac 1 a z$. Now for $r >0$ small enough we have $z^n < h(z)$ for $z \in \partial B_r(0)$, and for $w$ with $|w| < |z|^n - |h(z)|$ we get by Rouches theorem that $g(z)=w$ has $n$ solutions in $B_r(0)$. But unfortunately these solutions don't need to be in the right half plane. Any ideas how I could improve this argument.
I suspect the answer to be $n=1$, since then $f(z) = 1/z$ works. For higher orders I haven't yet found solutions.
Assume the pole is of order $n$. Then we can write $f(z)=\left(\frac{h(z)}{z}\right)^{n}$ near $z=0$ for some analytic $h$ with $h(0)\neq0$.
Let me call $\Omega$ the open upper half disc. Call $G=h(\Omega)$ and $D_a$ the image of $\Omega$ by $z\mapsto az$. Observe that $D_a$ is just another open half circle with center at the origin.
Let $a^n$ be a complex number with $|a|$ very large, such that $\frac{h(z)}{z}=a$ has solutions $z_0$ very close to $0$. Therefore $G$ and $D_a$ intersect (at $az_0$ for example).
If $n>2$, then either $D_{aw}$ or $D_{a/w}$ also intersect $G$ at $az_0$, where $w=e^{2\pi i/n}$. In fact $$D_{aw}\cup D_{a/w}\supset D_a\ \color{red}{\leftarrow\text{ This covering thing is what fails for }n\leq2}$$
Therefore, either $b=z_0/w$ (or $=z_0w$ depending on which one had the intersection) is in the open upper half unit ball, and will give us $h(b)=awb$ (or $=ab/w$). So, $f$ is not injective in the open upper half unit ball, because $f(z_0)=a^n=f(b)$.
Therefore $n\leq 2$.
The pole can be of orders $1$ or $2$ as in the examples $f(z)=\frac{1}{z}$ and $f(z)=\frac{1}{z^2}$